20 Amazing Airbnb Vacation Rentals In The Berkshires, Massachusetts - Updated 2024

Alesha
Alesha 
Updated
| 8 min read

Ready to jet off to your next holiday? It is high time to consider The Berkshires. This is a region in the western part of Massachusetts with a booming tourism scene filled to the brim with music, arts, and an endless list of recreation. Discover artworks at nearby museums such as Norman Rockwell Museum and The Clark. Since it is a fantastic place to visit all year round, you can indulge in a beautiful blend of the authentic countryside and a hotpot of different cultures. Stand before vivid colours plastered on the rolling hills that look straight out of a painting. Explore countless restaurants and shops in Lee Premium Outlets. Whether you are travelling in a big group or with your significant other, check out this list of the best Airbnbs in The Berkshires, Massachusetts.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 06, 2024.

1. Scandinavian-inspired rustic cabin (from USD 120)

With a cozy, Scandinavian-inspired design, this two-bedroom cabin is a perfect retreat for guests as it’s close to several lakes, ponds, and hiking spots. Enjoy a rustic vacation in the cabin as you relax with a good book by the woodstove. The kitchen has a refrigerator, a stove, and an oven for easy meal preparation. Guests bringing young kids will be happy to know that there are children’s books, toys, and a highchair available.

Easily accessible, the cabin is only minutes away from Jacobs Pillow and five minutes to the swimming pond. Several hiking trails are only right across the street.

Stayed at this property?
Otis, Massachusetts, United States
21.57 km (13.5 mi) from Norman Rockwell Museum
399 reviews   Superhost Wifi Available
Entire cabin 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
had difficulties to connect to wi-fi but the hot spot of cell phone worked perfectly
the wifi was strong enough for long video calls
the sleeping quarters are aesthetic and comfortable most importantly everything was clean
i was working remotely and the wifi was strong too :) thank you
clean stylish and super cozy with all of the amenities of home
Cleanliness:
clean and well maintained
this place is a real gem --- so clean and cozy
clean and cozy thoughtfully designed and taken care of
very clean we like design and style
nicely built clean toasty woodstove to warm up by after a long day skiing
Host:
they were also quite responsive hosts
mike and anna were great hosts
mike and anna are very responsive hosts as well it's a special place
mike and anna were excellent hosts house is amazing great cozy design and excellent amenities
mike and anna are trustworthy hosts with great communication
Location:
cute cabin in a great location
a wonderful stay cannot recommend highly enough close to many wonderful spots (maple corner is a must-do)
Read more reviews

2. Four-bedroom cabin near Beartown State Forest (from USD 343)

Situated in 2 acres (0.8 hectares) of secluded land, this four-bedroom cabin is a great place to go for those who want some peace and quiet. It has a screened porch and an outdoor hot tub where you can relax with a nice drink. The fire pit outside also offers a place for guests to relax, tell campfire stories, or simply roast some marshmallows. The cabin’s modern kitchen is furnished with a refrigerator, a stove, an oven, and granite countertops.

In terms of places you can visit, the cabin is close to the Appalachian Trail in Beartown State Forest and a kayaking and swimming spot at Lake Garfield.

Stayed at this property?
Monterey, Massachusetts, United States
12.93 km (8.1 mi) from Norman Rockwell Museum
245 reviews   Superhost Wifi Available
Entire cabin 4 Beds 7 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 7

Top guest reviews
Amenities & Room:
this classic log cabin has spectacular views a stream a well-maintained hot tub two fireplaces and a terrific kitchen
amazing cabin in the woods with all the amenities great kitchen for cooking and hot tub for relaxing
the kitchen and grill helped all of our foodie dreams come true and we made some amazing meals
the cabin was extremely comfortable and well equipped
the house was very comfortable for our needs
Cleanliness:
really nice place very clean and well equipped
super clean very comfortable also for kids
it was private clean and well-appointed
the cabin was also very clean which was greatly appreciated
plenty of space clean and fully equipped
Host:
david was a very responsive host and was very helpful when we had questions
the host is extremely responsive and helpful
on top of our great stay david and nicki were wonderful hosts who responded quickly to my questions
very responsive owners
david and nicki are great hosts communication is top notch
Location:
) and the location is fantastic
close to amazing dining but far enough away to feel secluded
great place to stay located perfectly
amazing upscale log cabin close to multiple berkshire towns
truly is home away from home perfect location for a quiet relaxing get away
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3. Enchanted Tiny Tower (from USD 228)

Describing itself as a whimsical and romantic tower, this two-storey tiny house provides a romantic and storybook-like aesthetic to its guests. It has an upstairs chamber with a canopied bed that provides a breathtaking view of the sky, pond, and trees which makes for a romantic evening. The kitchenette is equipped with a Ninja Foodi and microwave. Outside, guests can relax in the gardens, lily pond, and a running brook.

Finally, the tiny house is only 15 minutes away from the various shops and attractions in Stockbridge, Great Barrington, Lee, and Lenox.

Stayed at this property?
Tyringham, Massachusetts, United States
10.57 km (6.6 mi) from Norman Rockwell Museum
287 reviews   Superhost Wifi Available
Tiny home 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the fireplace bedroom with the sky view heated bed was amazing
wonderful spot for a getaway cozy and warm magical autumn retreat
however it was the perfect size for 2 and we loved that it was little and cozy
Cleanliness:
the place was amazing very clean
sparkling clean and plenty of little touches that were great
this place was perfect beautiful clean cozy and very covid safe would definitely recommend
Host:
owner was easy to contact and very responsive
the grounds were absolutely unique and stunning and the hosts were very accommodating and helpful
the hosts were very responsive and left a thoughtful note and welcome basket for us upon our arrival
the previous owner had hundreds of positive reviews on this place and i just really don’t understand it
hosts were responsive space was lovely + whimsical + we enjoyed very much
Location:
cute and special place for a weekend away
this place is so cute it really is tiny but in a cute cozy way
we loved exploring the grounds + the overall location is so convenient for exploring lenox/great barrington etc
this was a very cute and unique place to spend a couple of days
fantastic stay and a very unique place
Read more reviews

4. Residential home with breathtaking views (from USD 624)

This four-bedroom residential home offers breathtaking views to its guests while they sit by the fireplace. Gaze out the home’s windows and see the wondrous mountains and lake as well as the amazing sunset.

The great room has a spacious open floor design that’s made to ensure that guests can entertain themselves with the DVD player, movie collection, stereo system, and various board games provided by the owners. The kitchen boasts stainless steel appliances and a large island that seats six people. There is also a family room that is furnished with a large sectional sofa, a TV, a DVD player, and an Xbox 360.

Centrally located, the home ensures that guests will not have a hard time accessing the various attractions around them as it’s only 10 minutes from Butternut Ski Area and Tubing Center and 20 minutes from Great Barrington.

Stayed at this property?
Great Barrington, Massachusetts, United States
18.07 km (11.3 mi) from Norman Rockwell Museum
197 reviews   Wifi Available
ENTIRE HOME 5 Beds 9 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 9

Top guest reviews
Amenities & Room:
couches and chairs were all so comfortable
the house is decorated to perfection- luxury linens big comfy furniture fully stocked kitchen
cell phone service worked okay but best via wi-fi-calling
spectacular views the house is beautiful and very comfortable for a group of 8
the large open kitchen/dining/living space with incredible views of lake garfield was the best part of the house
Cleanliness:
so clean and beautiful
very clean and well appointed
the home is beautifully decorated and very clean making our stay even more comfortable
Host:
johanna was a great host
our host johanna was very responsive and accommodating to our requests
responsive host and beautiful home
johanna was quick and responsive with all of our questions
johanna was extremely responsive to our questions
Location:
loved the location
great location to tour around the berkshires
location was great to get around to different things
very relaxing atmosphere yet close to berkshires attractions perfect
this home and location are amazing
Read more reviews

5. Residential home with a private community dock (from USD 298)

Prepare for a lakeside vacation in this two-bedroom residential home. It boasts a private community dock where guests can either go fishing, swim in the lake, or paddle around the lake with a canoe provided by the owner. The home’s large deck and patio space offer a great place for guests to sit down and relax with a nice drink. The kitchen has a refrigerator, a freezer, a stove, an oven, a coffee maker, and a dishwasher.

As for nearby attractions, the home is only a five-minute drive away from Great Barrington and it various shops, restaurants, and attractions.

Stayed at this property?
New Marlborough, Massachusetts, United States
14.06 km (8.8 mi) from Norman Rockwell Museum
120 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
all the amenities we needed where there including good wifi
we stayed in mid-july and the air conditioning works wonderfully
importantly the mattresses were really comfortable
newly renovated clean very comfortable furniture and beds and in a prime location
great place very well appointed excellent kitchen and open living room kitchen plan
Cleanliness:
this house was extremely clean comfortable
very clean and well appointed for the space
clean and comfortable with great lighting
it’s modern clean and super comfortable
extremely clean accommodations pet friendly with beautiful porch and fire pit
Host:
mitchell was the perfect host
mitchell is a great host
mitchell is a great host
mitchell was great with answering questions and was incredibly helpful
he was quick to respond to any questions we had and was super helpful
Location:
the location is great too very close to a lake
great location for hiking or skiing
loved the location and the lake
in an ideal location close to downtown and hiking
a wonderful getaway in a perfect location
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6. Octagon chalet for a luxurious experience (from USD 296)

Luxurious doesn’t even begin to describe this holiday home. It sure is one of the best lodgings in the Berkshires and comes with a hefty price tag too. Splurge for the ultimate vacation of your life and pick this octagonal chalet as your retreat. The main living area is surrounded by floor-to-ceiling glass walls and is equipped with a fireplace. There’s also a modern kitchen with complete cooking equipment. A spacious outdoor deck with a fireplace, a grill, and plenty of seating are available too!

Stayed at this property?
Otis, Massachusetts, United States
21.85 km (13.6 mi) from Norman Rockwell Museum
336 reviews   Superhost Wifi Available
Entire chalet 2 Beds 4 Guests 1 Bedroom 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
this cozy home puts you in the middle of nature with its 360* views but with modern comforts
the ceiling fan plus the cool night breeze was perfect for us
the octagon tree house was beyond expectations simple put it was beautiful cozy peaceful and must to experience
amenities are superb: wonderful kitchen comfy beds sweet artistic touches and more
the space is tranquil and cozy with thoughtful touches everywhere
Cleanliness:
it was sparkling clean and the communication was easy
what a lovely relaxing clean retreat
super clean and lots to do in the area
this place is very clean private and intimate
clean and felt at home
Host:
the host was amazing
great place and really helpful host; would definitely recommend
katherine was an amazing host quick to responded and super helpful
the host provided everything we could have needed and more highly recommend
katherine provides good clear directions and is very responsive
Location:
location location location perfect setting
the house and location are beautiful
unique space with beautiful outdoor area in a convenient location
close enough to the faster paced towns and far removed enough to enjoy peace and quiet
lovely views and isolated this is the perfect place to just get away from it all and relax
Read more reviews

7. Eco-friendly home in the mountains (from USD 298)

Have a luxurious retreat in the mountain when you stay in this classy and elegant modern home with eco-friendly and energy-efficient amenities. With two minimalist-like bedrooms and two Murphy beds in the loft, eight people can sleep here comfortably.

If you’re in the Berkshires to ski or hike, consider spending a few more days just to have a staycation in this stunning home. With high ceilings and tall windows, the modern farmhouse-style kitchen and living area is the perfect spot for cuddling up and watching the day go by outside.

Stayed at this property?
Lee, Massachusetts, United States
4.94 km (3.1 mi) from Norman Rockwell Museum
202 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
overall the house just has a cozy light-filled happy feel
Cleanliness:
clean charming very fun place
the house is beautiful and impeccably clean
very clean and open feel to the house
this house was truly spectacular clean stylish and perfect
the place was exactly as the pictures show and the place was very clean on arrival
Host:
truly amazing hosts and space
mccaela was a lovely host very responsive and left a gift basket that we so appreciated
amazing home amazing hosts wonderful town and area
the hosts are absolutely lovely - super helpful responsive and warm
host was very responsive when we had a question
Location:
it's a great location
the location is amazing to so many great places in the berkshires
the central location made it easy to visit lots of places on our list
mccaela’s place is everything we could have hoped for
i highly recommend to anyone just looking for a nice place to get away and chill
Read more reviews

8. Rustic cabin with luxurious amenities (from USD 260)

Treat the whole family to a luxurious accommodation in the Berkshires with this four-bedroom cabin for eight people. Located in Otis, the main level is where you’ll find the couches and the fireplace, along with the kitchen complete with cooking equipment. There’s a screened-in deck with a lounge and a dining area, perfect for savoring your morning coffee or having an intimate dinner party. Outside there’s a bonfire area with Adirondack chairs, where you can swap stories with your loved ones and just enjoy being surrounded by nature.

Stayed at this property?
Otis, Massachusetts, United States
21.62 km (13.5 mi) from Norman Rockwell Museum
53 reviews   Superhost Wifi Available
Entire cabin 5 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the furnishings are lovely and comfortable as is the outdoor seating and firepit
this house is both well-stocked and no-fuss relaxing with comfortable seating
an amazing stay the space was larger than we expected and very comfortable for a group of 6
all of the rooms are nice and spacious with very comfortable beds
Cleanliness:
very clean and tranquil
her home is clean cozy and has everything you need to enjoy yourself
Host:
lindsay was attentive and responsive
lindsay was always available for all questions and very helpful thank you for your hospitality
Location:
what a beautiful location a beautiful house in the woods to enjoy time away
the location was great for hiking walking and exploring nearby towns
highly recommend this place if you want a break from the city
the house is sparkling clean beautifully decorated and a great location for exploring the berkshires
Read more reviews

9. Massive farmhouse with fireplace (from USD 390)

This stunning and restored farmhouse dating back to the 18th century is so spacious that its 8 bedrooms can house up to 15 guests. During your stay here, you will inevitably draw your attention to the 1770’s fireplace that exudes character. While there is no central air-conditioning in this historic Berkshire summer rental, the bedrooms come with their own air-conditioning. The kitchen is fully equipped with all the materials you might need for cooking, including pots, pans, and a stove. Kickstart your day with a delicious cup using the coffee maker. The television also comes with cable, making it perfect for rainy nights as you gather around and watch the group’s favourite shows while a fire keeps you warm. The bathroom will be provided with shower gels, hangers, and shampoos, and you will be able to find extra pillows and blankets. Be sure to check out the garden and backyard to enjoy a sunny afternoon.

Stayed at this property?
New Ashford, Massachusetts, United States
38.29 km (23.8 mi) from Norman Rockwell Museum
165 reviews   Superhost Wifi Available
ENTIRE HOME 8 Beds 15 Guests 8 Bedrooms 3 Bathrooms

Accommodates: 15

Top guest reviews
Amenities & Room:
we loved the big kitchen the beds were super comfortable we have all the amenities we could want
plenty of space beautiful bathrooms plenty of excellent kitchen tools/utensils 8 terrific rooms to choose from
easy to cook in with multiple kitchens
we joked about only actually seeing a fraction of the rooms
so fun to look around all the rooms in the house
Host:
owner very responsive to questions
host was excellent and efficient communicator
thomas is a wonderful host
easy check in and helpful host - thomas answered questions rapidly
host was extremely helpful and quick to respond
Location:
lovely location on a large estate
the house is great great location for williamstown and north adams
the location is very beautiful and it was a great space to gather with friends
a perfect place to relax with beautifully maintained grounds
this was a fabulous place for our "girls weekend" away
Read more reviews

10. Historic house with a touch of modernity (from USD 150)

This beautiful and historic house boasts an antique style mixed with a hint of a modern vibe. It is found at a convenient location just a stone’s throw away to The Berkshires attractions and Hudson Valley. Enjoy a large bedroom that comes with a private attached bath. As you enjoy the best of the countryside in The Berkshires, rest your heads on fresh linens fitted with clean and sanitized blankets and duvets.

Stayed at this property?
Hillsdale, New York, United States
19.26 km (12.0 mi) from Norman Rockwell Museum
252 reviews   Superhost Wifi Available
PRIVATE ROOM IN HOME 1 Bed 2 Guests 1 Bedroom 1 Bathrooms

Accommodates: 2

Top guest reviews
Amenities & Room:
charming farm meets contemporary home with comfortable furniture and eclectic furnishings/decor
lovely artwork comfortable furniture great coffee and snacks and very clean
my room had an ensuite bath with a clawfoot tub a comfortable bed and a window a/c unit
comfortable room with large closet ensuite bathroom great bed
breakfast was delicious and there was always hot coffee
Cleanliness:
very clean and nice house
they made sure to follow all cleaning protocols and the space was very clean and cared for
extremely hospitable and clean
bathroom nice and spotless
our room was clean and cozy funky shower fluffy towels and loads of wonderful books
Host:
daniel is a great host
you certainly don’t find this kind of hospitality everywhere
very hospitality hosts and beautiful home
the owners are helpful and responsive
they are delightful hosts with an eye for design and hospitality
Location:
the location was ideal for us
ideal location close to great barrington
a perfect location
great location great value
perfect location to access the berkshires
Read more reviews

11. Cosy cottage nestled in the woods (from USD 125)

If you are looking for some time away from the hustle and bustle of city life, you should consider this cosy cottage that sleeps up to four. The accommodation comes with one aueen-size bed and one futon. Gather around the indoor fireplace and watch your favourite shows on the cable television here when the weather is too cold. Despite being nestled in the woods, you will find plenty of things to do around the area. There are many hiking trails for you to explore, so strap on your hiking boots and get going.

Stayed at this property?
Williamstown, Massachusetts, United States
35.42 km (22.1 mi) from Norman Rockwell Museum
162 reviews   Superhost Wifi Available
Entire cottage 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the cottage is cute and comfortable
exactly as listed- cozy the cottage is very comfortable well furnished stocked with supplies and clean
the kitchen is galley sized so not a lot of space but was wellequipped
the kitchen is small so we mostly used the outdoor gas grill which was a great amenity
the fireplace in the living room was amazing
Cleanliness:
great place very clean and unique
we were ultimately able to locate some clean fresh sheets in another cabinet
everything was clean and ready for our use
the house was super clean and had everything we needed for our stay
Host:
our host was super responsive and helpful
regina was a great host and responsive by phone/text
regina was gracious and communicative
regina was so communicative with anything we needed throughout our stay would definitely stay again
regina was uncommonly kind and flexible about adjusting my trip when we were delayed due to snow
Location:
it’s close to several delicious local restaurants
the location is excellent- close to town massmoca hiking skiing
the cabin is located just ~10 from downtown williamstown but is quiet and restful
we loved this little cabin and location/proximity were perfect for our needs
this was a great location to enjoy the berkshires
Read more reviews

12. Mountain-view home near hiking trails

This home away from home is a favourite among people who love going outdoors as it is also known as a hiker’s paradise. Explore the different trails that can be found just 5 to 10 minutes away. There are also many areas you can discover, including gorgeous rolling hills with lush greenery and authentic country roads. After an outdoor adventure, hop on the hammock to rest and drift off in the peace and quiet here. This home can accommodate up to four guests in rooms that come with twin beds and floor-to-ceiling-windows, allowing them to wake up to some of the most picturesque views of the mountains at The Berkshires. When it comes to whipping up a delicious meal to recharge, make use of a fully equipped kitchen that comes with an oven, a microwave, a fridge, and all the cookware you might need. Start your day right and brew a fresh cup of coffee with the coffee maker here.

Stayed at this property?
Williamstown, Massachusetts, United States
36.54 km (22.8 mi) from Norman Rockwell Museum
195 reviews   Superhost Wifi Available
Entire cottage 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the decor was spot on the bedding linens and furniture all comfortable and the house was immaculate
comfy beds beautiful views and lovely hosts
beautiful space and very comfortable beds
the house is beautiful and private with a great open kitchen
the evening campfire was a real treat the entire space was just adorable welcoming and comfortable
Cleanliness:
clean and everything you could want
house was charming clean and nicely stocked
joe’s place was sparkling clean
it’s beautifully decorated and was sparkling clean for us
joe's place was fantastic the place itself was really clean and very spacious
Host:
joe was a great host
joe was attentive and kind
) otherwise a lovely home with a lovely host
joe was very responsive to any questions we had
our hosts were helpful and responsive
Location:
great location for visiting the berkshires
what a wonderful place in a beautiful location
the location was just what we needed for a relaxing weekend away
fantastic space in a great location
very nice location lots of tips of what to do in the area
Read more reviews

13. Mountain-view home with sauna and hot tub (from USD 884)

With 6 spacious and comfortable bedrooms and 4.5 bathrooms, this stunning home can take up to 15 guests, making it an excellent choice if you are planning for a family get-together or travelling with your buddies. The house sits on a 38-acre (15 hectares) plot of land in the woods, against the backdrop of breathtaking mountain scenery. On cold days and nights, you and your loved ones would not have to fight for the fireplace, as there are four fireplaces with ample areas to hang out. If you are looking for the ultimate relaxation, hope into the sauna or hot tub and unwind. There are also many places of attractions that are just a stone’s throw away. Grab your skis and winter coats and head over to the Jiminy Peak Ski Resort, which is a quick nine-minute drive away.

Stayed at this property?
Lanesborough, Massachusetts, United States
28.35 km (17.7 mi) from Norman Rockwell Museum
87 reviews   Superhost Wifi Available
ENTIRE HOME 10 Beds 14 Guests 6 Bedrooms 4 Bathrooms

Accommodates: 14

Top guest reviews
Amenities & Room:
the only suggestion for improvement would be to install room darkening curtains or blinds in the bedroom
beautiful berkshire hills wildlife wifi made this place ideal to work and play
Cleanliness:
house is very clean and has plenty of space for activities
the house was very clean overall and it had everything we needed for our stay already
jon's house was great in every aspect; clean great spaces fully functional and in a great location
Host:
jon was very responsive
the owner and his caretaker were kind and responsive
the owner was very responsive and courteous
the care taker is amazing and super helpful
he and his caretaker jim went above and beyond to make sure we enjoyed our stay
Location:
it’s located down a dirt road in the beautiful berkshire hills very close to jiminy peak mountain resort
the property has nice hiking and the drive to town was very close by
wonderful place to get away and relax
great getaway location the area was beautiful the kitchen was well stocked and everybody loved the house
jon’s place is absolutely amazing
Read more reviews

14. Beautiful home with gorgeous waterfall views (from USD 264)

Retreat and unwind at this rustic five-bedroom, three-storey abode. This house is situated on 15 acres (6 hectares) of private forestland, making this an excellent choice for those looking for a getaway with nature. Huddle up and stay warm using the fireplace here while you look out into the dense forest encompassing the house. This historic house was built in 1910 and remodelled in 2011. Enjoy a new kitchen, a gas range, a gas furnace, and on-demand hot water. This house comes with three bathrooms with two showers. Located at an excellent location, you can grab your skis and drive 15 minutes to Jiminy Peak Ski Area, or 30 minutes to Bosquet’s Ski area in Pittsfield.

Stayed at this property?
New Ashford, Massachusetts, United States
36.47 km (22.7 mi) from Norman Rockwell Museum
86 reviews   Wifi Available
ENTIRE HOME 6 Beds 6 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the tv is old too but the internet worked well
the house was rustic (which i expected)but very comfortable
there were three bathrooms which was nice to have for 5 people
Cleanliness:
it was clean quiet and cozy
the house was clean and tidy with plenty of room for for 6 people
the house was beautiful and clean and had a lot to make our stay more comfortable
the kitchen was well supplied for cooking and the refrigerator very clean
Host:
elena the house manager is super accommodating and helpful
the host was unbelievably helpful and super responsive
elena the house manager was very helpful for specific questions we had
michael is a great host he responds immediately to any questions or concerns
quiet and scenic with thoughtful and attentive host/house manager
Location:
the location of the house was great
the location is superb and the house charming
the house is close to many attractions
the location was great and the area is quiet and beautiful
this rustic unique spacious house was the perfect location for the four of us to spend a week together
Read more reviews

15. Marvelous cottage near places of attractions

Situated on a quiet plot of land measuring 2 acres (0.8 hectares), this accommodation is the perfect location if you are looking to get away from the cacophony of city life. Grab your hiking shoes and explore the woods surrounding the cottage. There are two bedrooms with comfortable queen-size beds. The kitchen comes equipped with the necessary materials you might need to whip up delicious meals for a recharge. During your stay here, you will not run out of things to do. This Berkshire cabin rental is a quick drive away from ski areas Barrington Stage Company.

Stayed at this property?
Pittsfield, Massachusetts, United States
17.72 km (11.1 mi) from Norman Rockwell Museum
388 reviews   Wifi Available
ENTIRE HOME 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
very cozy good wifi and disney channel a plus
the cottage is rustic (with some nice artistic touches) and has all the necessary amenities for a comfortable stay
pauls place is a cozy cottage with a lot of natural light and beautiful views
clean and easy instructions on how to use ac heat wifi tv etc
very cozy space great for fall views
Cleanliness:
very clean and useful
comfortable beds and very clean
the house was clean and well equiped
paul’s place was amazing it was as advertised very clean and cozy
it was beautifully clean easy parking and easy check-in/out
Host:
paul was very helpful
paul was also very accommodating and responsive whenever i had questions
paul and lainey were very kind and helpful
paul was a great host - communicative accommodating and friendly
paul was so incredibly kind
Location:
close to all the local attractions
this was in a beautiful and convenient location to the attractions in the area
great cozy spot close enough to shopping but still feels private and quiet
super close to town and a very laid back atmosphere
nice place to stay in a great location
Read more reviews

16. Modern and rustic retreat near the lake

Perfect for family reunions or group outings, this modern lodging in the woods welcomes 12 guests in its 4 cozy bedrooms. There are two living areas with fireplaces, a fully equipped kitchen, and free Wi-Fi. You can set up some activities with your group in the main areas and have a group feast on the screened-in deck. The lake is a short walk from this vacation home, as well as the clubhouse, gym, playgrounds, and sports centers. Staycationing in the Berkshires is about to get so much more fun!

Stayed at this property?
Sandisfield, Massachusetts, United States
23.34 km (14.6 mi) from Norman Rockwell Museum
31 reviews   Superhost Wifi Available
ENTIRE HOME 7 Beds 10 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
great vacation home with tons of sleeping room and space that would be perfect for families
the kitchen is well-equipped and the bed and pillows in the room i stayed in were super comfortable
Cleanliness:
house was clean beds very comfy and kitchen had everything we needed
Host:
kelly was super responsive to all questions
and the people all around are extremely friendly
thanks kelly for being an amazing host we are already planning to come on spring for hiking
the binder is super informative and kelly answered any questions very promptly
Location:
the house has a great location to discover the berkshire area
the place seems perfect for a summer getaway as well
Read more reviews

17. Woodlands-view cabin with hot tub (from USD 148)

Splurge on an ultimate Berkshires experience with this modern cottage that’s ideal for five people. Its best feature, arguably, is the outdoor hot tub with a view of the open (but private!) yard and the towering trees. Inside is a bright living room with a TV and a spacious kitchen overlooking the outdoors. A fire pit and a propane griddle are provided as well. Guests of this home are welcome to use the canoe that’s docked on the lake which is a short walk from the property.

Stayed at this property?
Becket, Massachusetts, United States
22.49 km (14.0 mi) from Norman Rockwell Museum
332 reviews   Wifi Available
Entire cottage 2 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
the heater kept the whole place nice and toasty
the wifi signal was perfect and even reached out to the hot tub no buffering at all
we appreciated the condiments spices tea and kitchen supplies
the place is cozy plush and well-stocked and alison was an incredibly responsive and thoughtful host
Cleanliness:
walls needed to be cleaned and/or painted and countertops were clearly fraying from the bottom
the location was excellent and the cottage was clean and adorable
Host:
our host was prompt kind and courteous
alison was super communicative and a wonderful host
alison is a real super host and will take good care of you with excellent communication
alison was an excellent host with fabulous communication
alison was very responsive and sweet
Location:
great location for hiking
house felt secure and the lake was beautiful to walk around
awesome such a great place to get away and relax
super private in a quiet neighborhood in becket
we had an excellent stay at alisons’ place
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18. Luxurious house ideal for families

This fantastic accommodation is ideal for families as it can sleep up to 16 guests. This seven-bedroom, four-bathroom home is the epitome of luxury and tranquility. Enjoy ample space outdoors where the kids can run around while the adults can have fun at the bar. There is also a fully equipped kitchen that would make whipping up delectable treats for the family a breeze. Catch up on the family’s favourite games in the fully stocked game room equipped with dynamic games for all ages.

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Williamstown, Massachusetts, United States
40.51 km (25.2 mi) from Norman Rockwell Museum
21 reviews  
Entire house 11 Beds 7 Bedrooms 4 Bathrooms
Top guest reviews
Cleanliness:
) everything was sparkling clean
the house is clean spacious comfortable and tastefully decorated
the home was extremely clean and the temperature was very comfortable
it was clean and spacious making it an excellent spot to accommodate all 15 people
this large comfortable quiet clean home is just the perfect place for a large gathering
Host:
owner was very responsive and helpful
beautiful stylish spacious home julie was a great responsive host
julie was very responsive and we really enjoyed our stay
julie is an extremely responsive host - prepare for a very happy stay
julie was very responsive and worked hard to meet our needs
Location:
perfect location to access all the berkshires has to offer
location location location near to massmoca and the clark and lots of wonderful hiking and more
beautiful space in enchanting location
fantastic bedrooms huge back yard great location
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19. Stylish abode sprinkled with a modern chic design

This house was built in 1960 and boasts a mid-century modern design. Enjoy this recently renovated home that comes with state-of-the-art kitchens and baths. This vacation rental in the Berkshires can house up to four guests, making it the ideal choice for small groups that are looking to travel or couples wanting to be whisked away on a romantic trip. Here, you will find all the amenities and convenience you might need during your stay. Start your day with a fresh cup of coffee using the coffee maker in the kitchen and whip up the group’s favourite meals with the stove and oven. When it is time to retire for the night, enjoy the soft and fluffy pillows and hop on the premium king-size and queen-sized beds. There is also a barbecue pit here, making it the perfect activity to enjoy a gorgeous sunny afternoon.

Stayed at this property?
Lenox, Massachusetts, United States
7.64 km (4.8 mi) from Norman Rockwell Museum
100 reviews  
Entire house 2 Beds 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
check in was easy wifi worked great and nice to have an outdoor grill
the shower has an amazing view and the space is extremely clean and beautiful
it is nicely decorated and the king bed is very comfortable
place was great slightly smaller irl than the photos made us believe but great location clean and comfortable
we appreciated the soap supplies in the bathroom
Cleanliness:
clean and nicely decorated with some interesting touches
decent clean place 1 mile to town
what a great place highly recommend super clean full kitchen and clean linens
the house was extremely quiet and clean
it was incredibly clean - couldn't be cleaner actually
Host:
johanna the host was very helpful and responded quickly
johanna was an excellent host
host was was accommodating and really easy to reach out to an answered promptly
the host is great and place is amazing
joanna and chris are very responsive hosts
Location:
great location and great value
cute and very stylish with a great location in terms of access to hiking
spent a long weekend at this cute little house in a great location for exploring the berkshires
beautiful and cozy house in a great location
but good location and a hip little house
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20. Snug guest suite for six

You will find everything you need in this lovely accommodation. With three bedrooms, a fully equipped bathroom, and a common area that comes with a coffee bar, this suite has ample space for you, whether you are travelling in a small group or going big on your adventures. Enjoy a newly renovated second floor and gather around in the living space. For all your food preparation needs, this location comes with all the amenities you might need such as a refrigerator, a coffee maker, and a microwave. Step outside on the deck and patio for fresh air and let the sun hit your skin. This is an excellent choice of accommodation that you should consider in your search for the perfect stay.

Stayed at this property?
Lanesborough, Massachusetts, United States
31.2 km (19.4 mi) from Norman Rockwell Museum
156 reviews   Superhost Wifi Available
Entire guest suite 4 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
comfortable modern space with thoughtful collection of amenities
awesome view and very cozy beds
beds were cozy and a lovely compliment of amenities were available
they had a coffee/breakfast bar for us with a few extra treats that we enjoyed
the bed was super comfortable there were extra pillows blankets etc
Cleanliness:
super clean and spacious
it was meticulously clean
a clean quiet and relaxing space
the house was very clean and beautifully decorated
sparkling clean comfortable apartment for this group of four
Host:
the hosts are kind and extremely responsive
friendly hospitality at check in
awesome place with awesome hosts
the hosts were a lovely couple who were thorough generous and accommodating
barbara and randy were wonderful hosts
Location:
great location for ski lovers
awesome place close to everything
perfect location for skiing at jiminy
it was the perfect location for getting around to many nearby attractions
great location for a tanglewood weekend (about 30 minutes away)
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The best of The Berkshires

Explore the best of what The Berkshires in Massachusetts has to offer, from breathtaking views to fun-filled activities. With its rich culture, it’s no surprise that many visitors embark on their adventure here. Choose from a long list of things to do such as shopping, museum-hopping, and indulging in delectable delights. So, what are you waiting for? Begin your vacation today.

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Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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