Top 12 Airbnb Vacation Rentals In Pittsfield, Massachusetts - Updated 2024

Pala
Pala 
Updated
| 5 min read

Pittsfield, the largest city in Massachusetts, offers limitless things to see and do for travelers. It is an excellent destination to explore the rich history, savor delicacies in gourmet restaurants, and indulge in outdoor adventure activities. The town boasts some of the finest attractions in the regions, from state forests and ski lodges to museums. Berkshire Museum, for example, brings visitors together for a unique educational and innovative experience. The museum has collections from all continents. Outdoorsy tourists will love racing along the slopes of Bousquet Ski Area for an exciting adventure. Pittsfield State Forest is another wonderful option for your outdoor adventure. If you are planning to visit the city soon and in pursuit of homey accommodation, try out any one of these top Airbnb vacation rentals in Pittsfield, 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 March 07, 2024.

1. Family-friendly property with a kids' play area (from USD 200)

Have a wonderful time in this abode, where comfort, relaxation, and family fun come together, and pets are welcome. Spend quality time watching shows on a 55-inch high-definition TV equipped with Fire TV and standard cable. You’ll love the travel crib and clamp-on table seat high chair, making the little ones’ mealtime and bedtime a breeze. There’s no shortage of entertainment here, with toys and a kids’ play area in the basement.

WiFi lets you stay connected online and productive no matter where your adventures take you. Freshen up in the bathtub after a long day of exploration. Enjoy the covered seating area under the back porch, the perfect spot to enjoy a meal or read a book while living in peaceful surroundings. Gather around the backyard fire pit while sharing stories with family and friends.

Stayed at this property?
Pittsfield, Massachusetts, United States
15.25 km (9.5 mi) from Jiminy Peak Mountain Resort
45 reviews   Wifi Available
ENTIRE HOME 5 Beds 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
soft and comfortable - all mattresses were new and perfect
this home was so comfortable for a family of 7 4 adults and 3 young tweens
the dining room sat all of us to dine together and play games
Cleanliness:
clean well decorated and great communication
we really liked this airbnb it was very clean and comfortable and had a modern yet cozy feel
excellent hosts very nice and clean house in a great location
the home is clean and comfortable and communication with hosts was excellent
Host:
hosts are great very responsive and helpful
joann and kate were amazing hosts
Location:
the location was perfect for us
perfect place to stay for our get away to the berkshires
a lovely berkshires home perfect for a little suburbs getaway and still close to everything you could want
quiet neighborhood with a nice park at the end of the road
it was a good location for exploring pittsfield and doing some day hikes
Read more reviews

2. Serene and beautiful home

Stay in this beautiful house in a serene neighborhood surrounded by lush greeneries. You’ll feel right at home among the natural plant decorations that adorn the space. There is a 43-inch flat-screen TV equipped with Disney+ and Netflix, perfect for a night in with your favorite movies and shows. For a bit of old-fashioned fun, board games will keep you entertained for hours on end.

There is fast WiFi, making communicating with loved ones during your stay easy. When you’re ready to unwind, soak in the bathtub for a relaxing end to your day. With free parking on the premises, you can explore the area without the stress of finding a parking spot after returning home. Enjoy the large backyard hill, perfect for picnics or relaxing in the sun.

Stayed at this property?
Pittsfield, Massachusetts, United States
12.34 km (7.7 mi) from Jiminy Peak Mountain Resort
40 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 7 Guests 3 Bedrooms 1 Bathroom

Accommodates: 7

Top guest reviews
Amenities & Room:
our mattress was extremely comfortable
we recommend that the owners check out why the wifi was slow
the beds were very comfortable
the bathroom was large and beautiful
the bathroom and kitchen are perfect and all rooms are well appointed
Cleanliness:
house was great clean and comfortable
comfy beds clean home and great location
beautifully appointed clean and stocked with everything you need
the house was sparkling clean and very well equipped
the hosts provided terrific communication and the place was honestly spotless
Host:
hosts were very responsive
very friendly and helpful hosts
the host has introduced us to a great farm nearby where we found the best tomatoes
tanya thank you for hosting us we enjoyed the house so much
great location and house and the hosts are very communicative and helpful
Location:
perfect location in the berkshires
great place fairly close to everything we wanted to do
hydrangia house is a lovely place in a terrific location for access to the berkshires
this beautiful home is so close to so many amazing places
all in all a wonderful place to get away
Read more reviews

3. Apartment with great views (from USD 70)

Situated in the heart of the city, this four-person apartment in Pittsfield is set on a building’s third floor. It has its own private entrance of its own and offers excellent views. Homey and well-appointed, you will be close to nature, restaurants, shopping centers, skiing areas, and other entertainment options. Although the apartment is set off Highway 7, it offers peace and tranquility. The property features two well-furnished bedrooms and one-and-a-half bathrooms with updated amenities for a hassle-free stay.

Stayed at this property?
Pittsfield, Massachusetts, United States
12.93 km (8.1 mi) from Jiminy Peak Mountain Resort
151 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 4 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
loved the enclosed balcony and well-furnished kitchen
wifi did cut in and out a bit but overall was a great experience
the space has everything you need to feel comfortable
the apartment is beautiful well-equipped in the kitchen and bathroom
the space was private very comfortable and was the perfect winter getaway for us
Cleanliness:
clean and modern appointments
clean warm and spacious
the place was very clean and hospitable
very clean and tidy with a well stocked kitchen
this apartment is clean and nicely furnished and comfortable
Host:
the hosts were excellent
hosts were quick to respond and helpful when we had questions
the directions were easy and convenient and the hosts are very gracious
the hosts were always quick to respond and helpful
braden and andy are great hosts with a lovely space
Location:
a perfect location for being able to walk to downtown activities
perfect convenient location in pittsfield to stay
it's an older neighborhood having big grand houses close to each other
branden & andy’s place is really cute
it was quiet private and located fairly close to the interesting downtown of pittsfield
Read more reviews

4. Spacious and lovely house by the lake (from USD 389)

Come and enjoy your vacation in this spacious gorgeous house with your friends and family. The property is nestled between two lovely lakes and boasts fantastic views. This custom-built property can sleep up to 16 guests and features 8 well-appointed bedrooms, 3 full bathrooms, and 2 fully equipped kitchens. One of the best things to do in Pittsfield while staying in this abode is to visit Lake Onota, just a short walk from the property, where you can indulge in outdoor activities such as picnicking, fishing, boating, and swimming. The other lake is called Pontoosuc and is only a quick ride away.

Stayed at this property?
Pittsfield, Massachusetts, United States
8.39 km (5.3 mi) from Jiminy Peak Mountain Resort
159 reviews   Superhost Wifi Available
ENTIRE HOME 20 Beds 16 Guests 8 Bedrooms 3 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
this is a huge place with many beds two kitchens and all the amenities you need
it was great having two kitchen areas it allowed guests to split off into different areas
beds were comfy loved having two kitchens
there was plenty of space for everyone and had a bonus of two kitchens
two kitchens make cooking easy
Cleanliness:
props for good communication cleanliness and comfort
house per se is very clean and spacious well maintained
the house was very clean and we'll supplied with everything we needed like paper products linens towels etc
clean neat & large enough to hold an extended family
the house was huge clean and had such a great assortment of rooms
Host:
margaret was very responsive to any of my questions and was a wonderful host
margaret was very helpful and kind
the host was extremely helpful and accommodating and the area is absolutely beautiful
the place was perfect to host our group's retreat for the weekend
margaret was easy to work with and friendly
Location:
the house was close to two lakes which provided opportunity for daytime activity
the location is great; very secluded and a good getaway location for a gathering with the family
the location is great walking distance to onota lake and a 15 min drive to mount greylock
the location is very good it has 15-20 minutes driving to any food market or either skiing
we had a great time at this location
Read more reviews

5. Cute tiny cottage (from USD 190)

Quiet and peaceful, this cute tiny bungalow rental in Pittsfield is suitable for up to six persons and offers views of Richmond Pond. You will be able to enjoy amazing sunrises from this cottage. There are two bedrooms with three squishy beds and a modern bathroom. The property is a 15 to 20-minute drive from attractions such as Norman Rockwell Museum, Shaker Village, and Tanglewood. Come here for a comfortable stay and return home with a bagful of happy memories.

Stayed at this property?
Pittsfield, Massachusetts, United States
16.11 km (10.1 mi) from Jiminy Peak Mountain Resort
79 reviews   Superhost Wifi Available
Entire bungalow 3 Beds 7 Guests 2 Bedrooms 1 Bathroom

Accommodates: 7

Top guest reviews
Amenities & Room:
wifi works perfect
wifi worked great
easy stay beds and furniture were very comfy
the house accommodated 5 comfortably and had great coffee and wifi plus fire tv
the kitchen has all necessary tools to prepare a nice meal
Cleanliness:
clean and sweet place
the lakehouse itself was incredibly clean and comfortable
it is clean comfortable and well-equipped
extremely clean and well kept with lots of thoughtful touches
clean home near a beautiful lake
Host:
)the hosts were very friendly and we appreciate their hospitality
the hosts were friendly and communicative-they also left delicious pastries and cider for us
dave and vicki are gracious generous and thoughtful hosts
vicki is very responsive and always ready to help
always a quick response from dave and vicki and super helpful( above and beyond what you would expect)
Location:
close to water in easy to walk neighborhood
the location of dave & vicki's house is great
the location was great and the neighborhood was very peaceful
their lake house is beautifully located in a quiet setting
very nice to walk around the neighborhood and the kayaks were great
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6. h-century guest cottage with modern amenities (from USD 249)

Ideal for a maximum of four guests, this well-appointed two-storey cottage can assure you of a peaceful and relaxed stay. You can easily access Tanglewood as well as other attractions such as fine-dining restaurants and skiing areas while staying here. The property is loaded with a string of modern facilities and amenities so that you don’t have to compromise on the quality of your stay. Although it was built in the 19th century, it has been remodeled to meet the requirements of modern travelers.

Stayed at this property?
Pittsfield, Massachusetts, United States
15.16 km (9.5 mi) from Jiminy Peak Mountain Resort
86 reviews   Wifi Available
Entire cottage 3 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
really appreciated the extremely quiet and effective split ac along with the luxury shower
we were able to do some work at the breakfast table and enjoyed great wifi
first all of the reviews that you read about the comfort of the bed are 100% accurate
the 2-level house is beautifully renovated with a lovely kitchen complete with high quality appliances
michael provides floaties so we could relax read listen to music while in the pool
Cleanliness:
first the place is extremely clean and updated
the bed was super-comfortable and the unit was very clean and comfortable
the house was clean and comfortable as well as interestingly designed within a historical building
everything was very clean and the cottage is all new and modern
Host:
beautiful property and accomadations and great hosts
our hosts were so welcoming and the adjacent pool was just terrific
michael is a great host super helpful and prompt in any questions we might have
michael was a gracious host and replied promptly to any questions
both michael and his son were great hosts and made our stay very relaxing
Location:
the location was perfect
ideal location to hit all the area has to offer
the location as far as a headquarters for the area is perfect
we would definitely come back and recommend this place to others
Read more reviews

7. Quiet country cottage near attractions

Surrounded by lush green woods, this quiet country cottage is a stone’s throw away from attractions such as Barrington Stage Theater, Tanglewood, and Ski areas of Pittsfield, Massachusetts. The cottage was constructed more than 100 years ago, yet offers you all the modern amenities needed for a comfortable stay. Cozy and clean, it boasts two nicely done rooms and a bathroom with modern fittings. The accommodation is ideal for outdoor activities such as cross-country skiing and hiking. It is also close to conveniences such as restaurants and a convenience store.

Stayed at this property?
Pittsfield, Massachusetts, United States
12.91 km (8.1 mi) from Jiminy Peak Mountain Resort
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

8. Beautiful lakefront home (from USD 400)

You can stay only a few feet from the water when you book this lovely lakefront home with a host of updated amenities. Boat rentals are available at a nearby marina so you can enjoy a leisure boat ride with your companions. The cabin offers accommodation for a maximum of 12 guests ideal for a large family or a group of friends. It is located in proximity to restaurants, cultural offerings of Berkshire, and skiing areas. The brand new kitchen is fully equipped so that you can prepare your meals anytime.

Stayed at this property?
Pittsfield, Massachusetts, United States
6.73 km (4.2 mi) from Jiminy Peak Mountain Resort
31 reviews   Superhost Wifi Available
ENTIRE HOME 8 Beds 12 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
large deck overlooking lake with lots of amenities -- central ac strong wi-fi 3 bathrooms grill kayaks
it was so peaceful sitting on the comfortable couch while watching the beautiful lake view
the view from the living room overlooking the lake is outstanding
very comfortable for our group of 10
Cleanliness:
jay’s house is beautiful modern and extremely clean
house was perfect lots of room clean and comfortable
this is a lovely clean well-appointed home on a beautiful spot on the lake
the house was clean all the details were communicated perfectly and it was a totally awesome weekend
bedrooms and bathrooms are clean
Host:
host and property manager were very responsive
the owner and the lake house manager were a great host and very responsive
jay and the house manager were very helpful and gave us everything we needed
jay is a great host check-in is easy and the house was sparkling clean
Location:
place was great and lake front location was just perfect for a quick getaway with our family and kids
Read more reviews

9. Beautifully renovated farmhouse (from USD 101)

Stay close to a string of conveniences such as a hospital, a pharmacy, and a shopping center by booking this lovely renovated farmhouse fit for two guests. Although the farmhouse was built in 1850, it has undergone a complete renovation so that you will not miss any essential facilities. A modern fully furnished kitchenette will help you cook as you please. Enjoy free parking space for your vehicle just outside the door. The host also provides a barbecue facility for your enjoyment.

Stayed at this property?
Pittsfield, Massachusetts, United States
11.49 km (7.2 mi) from Jiminy Peak Mountain Resort
41 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
it was cozy and a minutes walk to great coffee and breakfast
our stay at duane’s place was great the apartment was a perfect size for two people
Cleanliness:
nice and clean
the apartment was clean quiet and comfortable
comfortable and clean place with everything you need
an extremely clean and quiet space for relaxation
squeaky clean newly renovated space lots of room
Host:
duane and sheila are also wonderful hosts
duane and sheila were great hosts and were wonderful to chat with
duane and sheila were great hosts
duane and sheila are great hosts
the hosts are accessible if needed and were willing to help as needed
Location:
close to many restaurants (walking distance) as well as centrally located for area attractions and day trips
easy walk to good places to eat in pittsfield
we had a lovely stay and would absolutely choose their place again
perfectly renovated flat in the rear of a house very closed to the main street
a great place to stay
Read more reviews

10. Cozy studio for two (from USD 53)

The studio is ideal for any person who is planning to relax and rejuvenate after a hectic week of work. It is also a haven for hikers and can accommodate two guests at a time. Although the property is not set in the best of localities, it is still comfortable and homey and offers picturesque scenery around without breaking the bank. The locality is safe and close to several attractions in Berkshire. The property is perfect either for a long-term stay or for a short visit.

Stayed at this property?
Pittsfield, Massachusetts, United States
11.29 km (7.1 mi) from Jiminy Peak Mountain Resort
133 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 0 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
it had what you’d expect like wifi tv kitchen washer/drier etc
full electric reclining leather couch xbox 360 2 flatscreens (1 smart tv) etc
) the bed area and couch are nice and comfortable with two tvs (i never used)
there’s a washer/drier a good tv with streaming and an xbox and a kitchen
the water bottles and breakfast food is a nice little touch as well
Cleanliness:
it was very clean and tidy
it’s decently clean but the shower just doesn’t really feel clean to me
the apartment itself was very clean and felt extremely secure
it’s quiet clean and warm
clean nice atmosphere and a lot is provided for
Host:
david was s a very kind host
david is a great host
david was so helpful and played the perfect host
a great host and a great place
lovely spot with a super thoughtful host and a great value
Location:
great space in a convenient location
great location everything we needed was 30 minutes or less
great place to stay close to everything great value
great place to stay great value close to everything
perfect for location near downtown pittsfield and very spacious
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11. Beautiful private room in villa (from USD 100)

Situated in a quiet neighborhood, this century-old cottage is rich with history. The owners have renovated it carefully so that it retains its original old-world charm. Perfect for two guests, it comes with a nicely done bedroom and one attached private bathroom. The room is spacious and cozy while a big private yard can be accessed for relaxing and reading books. It is a bed and breakfast property in Pittsfield where you can start your day with delicious food every morning and use the kitchen to whip up a quick meal.

Stayed at this property?
Pittsfield, Massachusetts, United States
13.23 km (8.3 mi) from Jiminy Peak Mountain Resort
147 reviews   Wifi Available
Private room in villa 1 Bed 2 Guests 2 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
our room and bath were very comfortable
spectacular house and an extremely comfortable bed in the arden room
we slept peacefully in the comfy king-bedded arden room
breakfast by the fireplace was a real treat
such a beautiful bed and breakfast
Cleanliness:
the place was as advertised and very clean and comfortable
the rooms are tastefully decorated clean and roomy
private bath and everything was clean
the place is spotless and beautifully decorated as was our room (the arden)
i stayed in the arden room and it was clean with comfortable bed and linens and quiet
Host:
wonderful hosts who care about their guests
hosts were a great pleasure
the hosts are knowledgeable and very friendly
ken and laurie were great hosts
hosts were very good about communicating
Location:
fantastic location and a really unique property
peaceful and secluded yet close to the town centre
the property is exquisite the location is walking distance to downtown attractions and restaurants
pictures don’t even come close to what edmister feels like
edmister house was great and close to everything tanglewood kripalu etc
Read more reviews

12. Spacious colonial-style house

Spacious and comfortable, this colonial-style home is suitable for up to seven guests at a time and enjoys a central location in Berkshires. The property boasts four beautifully decorated bedrooms and two full bathrooms. There is a big front porch where you can relax with a cup of coffee or any of your favorite drinks. The property also has a huge background patio with a couple of barbecue grills and fire pits. A spacious dining table can comfortably seat eight people for a delicious meal. You will be close to Lanesborough, Tanglewood, and several hiking trails while staying here. Other Pittsfield attractions such as Jacobs Pillow, Berkshire Theater Company, and Colonial Theater are also nearby.

Stayed at this property?
Pittsfield, Massachusetts, United States
11.68 km (7.3 mi) from Jiminy Peak Mountain Resort
31 reviews   Superhost Wifi Available
Entire residential home 4 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
we loved the huge sofa with large tv screen
it was nice that there were multiple places to eat: kitchen formal dining room and tables outside
Cleanliness:
house was clean and tidy
house was very clean and backyard was so enjoyable
the house is large clean and comfortable with 4 bedrooms and 2 bathrooms and a recently updated kitchen
the house was clean and provided us with everything we needed for our stay
Host:
the hosts were incredibly quick to respond gave local tips and were very kind
host was very helpful and responsive - answered questions incredibly quickly before booking and during our stay
Location:
the location is also excellent
if you need to travel anywhere it’s also close to highways which is super handy
the neighborhood is also quiet and lovely which makes for perfect bonfire nights
Read more reviews

Enjoy a home-away-from-home experience in this huge city

During your trip here, don’t miss out on any attractions that can be explored in and around this big city. Check out these Airbnb vacation rentals in Pittsfield, Massachusetts, if you wish to enjoy a home-away-from-home experience. If you want a fun-filled getaway, the best ski resorts are in the Berkshires.

Stayed at this property?

Frequently asked questions about the top Airbnb vacation rentals in Pittsfield, Massachusetts

1. Which Airbnb vacation rentals in Pittsfield have a hot tub?

If you want to stay in Pittsfield, whether for business or leisure, stay at this spacious and lovely house by the lake, where you can ensure that you’ll have a wonderful experience with a hot tub available for your unwinding.

2. Which Airbnb vacation rentals in Pittsfield have parking?

This apartment with great views, this spacious and lovely house by the lake, this quiet country cottage near attractions, and this beautiful private room in the villa all have parking available for their guests’ convenience.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Pala Sen is an avid follower of travel and health updates, current affairs and entertainment news from all across the world and writing is a passion for her. She had been previously associated...Read more

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