10 Best Lakefront Rentals In Berkshires, Massachusetts

Isabela Marie
Isabela Marie 
Updated
| 5 min read

In today’s bustling digital age, it’s quite easy to overlook the simple beauties that our world still offers, and not afforded to us behind the screen. Berkshires, a small rural region peppered with small villages that reflect a time long forgotten through their architectural landscape, has been a popular destination for outdoor enthusiasts.

For Moby Dick enthusiasts, Herman Melville’s Arrowhead is a must-visit destination that’ll allow you to explore the former home of the author. As Berkshires is known for its natural landscapes, you wouldn’t want to miss Monument Mountain or Berkshire Botanical Garden. If you’re up for a little lesson on art, science, and history, then make your way to the Berkshire Museum. Continue reading for the best lakefront rentals in Berkshires, Massachusetts, for stays in this beautiful region.

We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to a lake. The image galleries get refreshed with the latest updates regularly. They were last updated on March 13, 2023.

1. Rustic lakeside house, Richmond (from USD 250)

Looking to experience a more sylvan experience? Then this wonderful cabin over at Richmond will surely make it seem like you were transported to a much simpler time. With its interior design evoking a rustic lumberjack aesthetic, you will surely love the amazing craftsmanship of its wooden furniture.

Perfect for a summer fishing getaway, the property also offers the usual lake house amenities such as kayaks, rowboats, and even a deck to spend a nice relaxing summer day fishing. It also comes equipped with three air conditioners, one for each room, to cool you off after a day spent outdoors.

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13.89 km (8.7 mi) from Norman Rockwell Museum
68 reviews   Wifi Available
House 7 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 7
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
living room has 2 glass walls and wonderful woodsy view
there was a nice front porch with comfortable seating as well as tables and chairs for meals outside
the cabin comfortably fit the three of us with plenty of room had we been a bigger group
very nice and open living room
what more can you ask for? the beds were very comfortable and too many other touches to name
Cleanliness:
everything was very clean
very clean well stocked and laid out
we really like the property very clean
the cabin was comfortable clean and well equipped
house is clean comfortable and largely as advertised
Host:
carol is helpful prior to arrival
the owner remained in touch throughout and was very responsive and helpful
the owner was extremely helpful in providing information for our arrival and stay
the owner was wonderful to work with from pre-reservation through the end of our stay
the host is very responsive and kind and you couldn't ask for a better retreat
Location:
close to great hiking trails
and stores close by for easy access
the house and location were both very picturesque
the location with proximity to lenox and west stockbridge and to many many local hikes was excellent
perfect location great neighborhood access to the water for kayaking boating etc
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2. Rustic home by the lakeside, Sherwood Forest (from USD 244)

This wonderful rustic home located in Sherwood Forest is aptly titled “Peace and Quiet On The Lake.” The quaint and picturesque house is perfect for anyone planning to experience the great outdoors. Boasting a private lake alongside kayaking amenities, this lakehouse will surely give you a unique experience.

The two-bedroom, two-bathroom property offers a number of basic facilities including internet, heating, linens and towels, as well as kitchen essentials. An amazing destination all year round, be sure to give it a shot and find the peace and quiet you definitely deserve.

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22.66 km (14.1 mi) from Norman Rockwell Museum
125 reviews  
House 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the deck off the loft is nice with room to comfortably sit 2
we loved the breakfast sandwiches and pizza from sherwood shoppe
the house was clean comfortable in a quiet relaxing setting with stunning views onto a small lake
we played games on the kitchen table as well as used the screened in porch and deck table
the house was cozy on a quiet picturesque lake
Cleanliness:
the house was very clean and cozy
it was clean peaceful and quiet
the cabin was very clean and we thought the inside was actually nicer than it looks online
the house was very cute clean and the setting beautiful and peaceful
the cabin was clean and very comfortable and justin was extremely easy to work with
Host:
the owner was very responsive and helpful
i can only say to the owner thank you sooo much
justin was very responsive and helpful
justin was very quick with responses leading up to our stay and helpful with the fireplace
owner is very responsive and house had everything you need and then some
Location:
location was good for area hiking and activities
fun location and as others have said must be incredible in the summer
great waterfront location with a dock which we fished off of all weekend and actually caught several fish
we skied at otis ridge and loved the short walk to the sherwood shoppe for dinner
that tells you something right there gorgeous house right on the water beautiful yard and location
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3. Lakeside chalet on Goose Pond, Tyringham (from USD 235)

A perfect destination for those who want to experience the lakes of Berkshires, this modern chalet offers five kayaks and even a Sunfish sailboat. Even if boating isn’t your thing, the location is still suitable for any nature lover. Just a 10-minute stroll will bring you to Appalachian Trail: perfect for a nice refreshing hike!

If you feel like doing a little shopping, the Premium Outlet Village is just a 10-minute drive away and offers a wide variety of shops and restaurants around the surrounding area.

The property comes equipped with basic electronic amenities such as Wi-Fi and a TV with satellite/cable channels. If you enjoy home cooking, the chalet comes with a small kitchenette and even a grill on the deck overlooking a gorgeous view. It also has both air conditioning and heating which makes it a perfect place to visit all year round.

Stayed at this property?

11.49 km (7.2 mi) from Norman Rockwell Museum
96 reviews   Wifi Available
chalet 5 Guests 1 Bedroom 1 Bathroom

Accommodates: 5
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
comfortable beds in alcoves including a twin bed up a small ladder
good wifi access and tv with raku with many channels including prime and netflix
a/c worked great on one really hot night and others the fans were all that was needed
kitchen set up for light cooking augmented by outdoor grill perfect for us
the beds are very comfortable the deck terrific for meals and the lakefront peaceful and inviting
Cleanliness:
the room was very clean and it had everything we needed
very clean and wonderful hosts
the loft had everything we needed and was clean and cozy
the lake is gorgeous and so clean and clear
the loft is rustic but very clean
Host:
our hosts were friendly and helpful
tim and gail are gracious hosts
gail and tim were wonderful hosts
gail & tim were wonderful and truly exceptional hosts
the hosts were extremely friendly and accommodating
Location:
appalachian trail near by a bonus perfect location and hosts
it might be good to make its location clearer
great location close to many wonderful museums and hiking opportunities
the loft did not disappoint the location is great
beautiful setting and close to several small towns and places to visit
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4. Serene waterfront house in the woods, Sherwood Forest (from USD 288)

If you are looking for a place that’s secluded, this private waterfront house is just for you. With just one other neighboring property, this tranquil home overlooking a clear and gorgeous lake would be perfect for a romantic getaway with that special someone.

The rental offers three spacious bedrooms and two bathrooms and makes its home in over 2 acres (0.8 hectares) of forested land. It has amenities that include air conditioning, TV, and Wi-Fi. A kayak and canoe are also offered so that you can take advantage of that amazing lake right by the property.

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23.05 km (14.4 mi) from Norman Rockwell Museum
98 reviews   Wifi Available
House 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Cleanliness:
it was impeccably clean with soft comfortable linens
the place is super clean and well equipped
place was spotless dogs had room to run around outside and play in the lake
house is super cute and clean and owners responsive to little snafu with immediate resolution
the location was excellent and the home itself was very clean and welcoming
Host:
host was great-very accommodating and responsive to questions
larry was extremely accommodating and very responsive to any questions about the home or the area
a big thank you to the owner for sharing it with us
owner provided a detailed and thorough overview which made the check in and acclimation process simple and easy
larry was very helpful
Location:
great location house was great
location was fantastic close to the outlets and not too far from ski butternut
the towns that are close are great
great place for a fall trip
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5. Romantic cottage overlooking Lake Buel, New Marlborough (from USD 251)

This cozy cottage overlooking Lake Buel is perfect for any couple looking to have the perfect lakeside vacation. The property boasts breathtaking views of the lake and surrounding forest no matter which room you’re in. The cottage is located just a few miles from East Mountain State Forest and Monument Mountain, offering perfect opportunities for a couple’s hike. Butternut Ski Area and Tubing Center is also nearby, allowing easy access to winter activities.

The cottage also comes with a host of amenities such as a fully furnished kitchen, free Wi-Fi, and three flat-screen TVs to keep you entertained on a rainy day. You should definitely try out this romantic cottage that offers stunning views second only to the smile of that special someone.

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14.0 km (8.7 mi) from Norman Rockwell Museum
55 reviews  
cottage 2 Guests 2 Bedrooms 1 Bathroom

Accommodates: 2
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
the deck furniture was superbly comfortable and allowed for reading lounging and gazing at the water
the kitchen is nice and large and the master bedroom is very comfortable and lots of closets throughout
the bed was extremely comfortable
Cleanliness:
it was amazingly clean and updated
very clean very cozy very private
very comfortable very clean and very lovely
the house is so comfortable and clean
the cottage is cozy clean and comfortable
Host:
the owner was kind and very responsive
called my contact and she was helpful
the owner was great and communication was prompt and easy
excellent communication with the host before our stay and a thoughtful welcome gift waiting for us
Location:
great barrington was fun and so close
nearby downtown great barrington was fun with lots of cute restaurants and shops
what an adorable cabin on a perfect location
loved it so relaxing and close to great barrington
a+++ it was a fantastic location for our yearly ice fishing weekend
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6. Spacious house near Pittsfield, Berkshire County (from USD 600)

Another fitting choice for those planning to bring quite a lot of people to their stunning lakeside getaway is this 2,500-square-feet (232.2-square-meters) house near Pittsfield. It’s newly remodeled and sleeps a total of 14, and its homey exterior coupled with a modern interior is sure to give you an unforgettable vacation.

Enjoy a night with the family over at the house’s deck that directly overlooks Lake Pontoosuc. The rental includes a host of amenities including two flat-screen TVs, a fully furnished kitchen, and even a modern fireplace perfect for those planning a winter vacation.

Stayed at this property?

24.31 km (15.2 mi) from Norman Rockwell Museum
69 reviews   Wifi Available
House 14 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 14
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
great place with great views comfortable and spacious
would appreciate 2 more dining room chairs
the rooms we all very spacious and the balcony off the master bedroom was a favorite spot
only suggestion is some additional seating and lighting in the living room thank you
the dining room-into-sitting room looking over the lake is breathtaking
Cleanliness:
everything is clean and new
very clean well maintained
clean great for larger groups
it is always perfectly cleaned and well stocked with toilet paper cleaning supplies etc
this was a very nice clean property
Host:
communication was always quick helpful and kind
Location:
great location and house was perfect
beautiful house well stocked great location
house is brand new great location on the lake and beautifully decorated
) full list of tv channels to choose from good location and very comfortable
) - i believe made it a perfect year round house and location
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7. Charming waterfront house overlooking Onota Lake, Pittsfield (from USD 242)

Thinking of bringing the whole family? Give this three-bedroom waterfront home a try. Located in Pittsfield and overlooking Onota Lake, the property can definitely provide a heartwarming experience for the whole family. Perfect for those interested in watersports and fishing, the house also comes with a deep water dock.

The property is also close to a number of tourist hot spots, such as Jiminy Peak for those ski lovers, golf courses, and theaters. The property’s gas fireplace, windows, and doors were all recently renovated to provide a cozy winter experience.

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21.64 km (13.5 mi) from Norman Rockwell Museum
64 reviews   Wifi Available
House 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
beautiful views from the upstairs sun room & from the downstairs covered deck
the view from the front room were breathtaking
the kitchen was well equipped and all the furnishings very very nice
kitchen well equipped & weber grill worked great
the view was gorgeous and the weather warm enough for us to enjoy the beautiful sun room
Cleanliness:
it was very clean and well organized
clean comfortable and nice decor
the house was clean everything worked
great house clean & comfortable
the house was sparkling clean and well equipped
Host:
the owner is pleasant and very helpful
owner was helpful and responsive
i thank the owner for sharing his home away from home with us
the owner went out of his way to ensure that our stay was most pleasant
bob was also very responsive during our stay
Location:
the location is terrific
the location was convenient and beautiful
perfect location for our time spent visiting family and friends
great location on a small peninsula on a large lake
great location convenient to lenox/tanglewood
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8. Modern house overlooking Richmond Pond, Richmond (from USD 478)

If your taste suits a more modern aesthetic, this newly renovated home in Richmond would be perfect for you. Coming fully furnished with a flat-screen TV, fully equipped kitchen, and elegantly designed furniture, the property is also located right beside the Richmond Pond.

This four-bedroom, three-bathroom house offers a number of amenities such as internet, air conditioning, and heating that make this modern slice of heaven perfect to stay in all year round.

Stayed at this property?

13.6 km (8.5 mi) from Norman Rockwell Museum
65 reviews   Wifi Available
House 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
we especially loved the light-filled rooms lake views and super-cleanliness of rooms furnishings and kitchen supplies
easy access to the lake and there was plenty of room for our two families
Cleanliness:
the house was extremely clean and very spacious for us
the house was modern well equipped and extremely clean and well cared for
Host:
jon was a great host
jon was a helpful and accessible host
owner is very easy to communicate with
owner jon was very responsive and super helpful
jon the owner was excellent to deal with
Location:
the location is beautiful the house very clean
the location on the water was beautiful and we enjoyed the kayaks and canoe every evening
quiet and peaceful area
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9. Six-bedroom house with a beautiful yard, Sherwood Forest (from USD 524)

This is a large, private lakefront home overlooking the peaceful Robinhood Lake. This spacious 6-bedroom and 3-bathroom home can sleep a total of 10 people and comes with everything you need from kitchen essentials to Wi-Fi. It even features a gorgeous lawn to host the perfect waterside picnic.

This peaceful property is also perfect for fishing with the serene Robinhood Lake being abundant in pickerel and bass. Far from other distractions and nuisances, the property is still relatively close to the tourist sites that Berkshire offers such as Jacob’s Pillow and Tanglewood.

Stayed at this property?

23.03 km (14.4 mi) from Norman Rockwell Museum
63 reviews  
House 10 Guests 6 Bedrooms 3 Bathrooms

Accommodates: 10
Minimum Nights: 2
Refund Policy :

Top guest reviews
Cleanliness:
nice clean lots of beds
the house was clean and well equipped
clean spacious and convenient couldn’t ask for more
house was very clean and open and airy with plenty of group for out group of 8
Host:
host is super responsive and friendly
we had a lovely stay and dori our host was wonderful perfect place for a large group
the beach area was perfect for the kids the house had plenty of room and very kid friendly
Location:
excellent location and excellent owners
the location is perfect for a family reunion
great location - easy to ski at butternut and nearby lee a great destination for restaurants
the location was a the perfect peaceful escape from the city
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10. Beautifully renovated home overlooking Pontoosuc Lake, Berkshire County

Thinking of bringing the whole extended family on a nice getaway? This house overlooking Lake Pontoosuc is definitely the way to go. With four bedrooms that can sleep a total of 12 guests and four bathrooms, this property can definitely handle a multitude of guests.

This lakeside house comes equipped with kayaks, a dock perfect for fishing, three flat-screen TVs, and even a gaming system. With loads of different activities for everyone to enjoy, the property also comes with a brand new kitchen and grill that’s perfect for preparing family dinners.

Stayed at this property?

24.79 km (15.4 mi) from Norman Rockwell Museum
72 reviews   Wifi Available
House 12 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 12
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Oops, this listing is currently inactive. Check out these alternative properties in the same location.
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Lakehouse getaways in Berkshires

Lakehouses are the perfect getaway for city dwellers looking to find a change of scenery. Often found in secluded areas, you can ensure yourself some peace and quiet in these accommodations. Don’t waste a second and book yourself that relaxing trip you deserve in Berkshires, now.

Stayed at this property?
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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Isabela Marie is a writer based in Manila, Philippines. As a former student journalist, she turns to travel writing as an enjoyable blend between her two favorite things.

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