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.
Top guest reviews
Amenities & Room:
living room has 2 glass walls and wonderful woodsy viewthere was a nice front porch with comfortable seating as well as tables and chairs for meals outsidethe cabin comfortably fit the three of us with plenty of room had we been a bigger groupvery nice and open living roomwhat more can you ask for? the beds were very comfortable and too many other touches to nameCleanliness:
everything was very cleanvery clean well stocked and laid outwe really like the property very cleanthe cabin was comfortable clean and well equippedhouse is clean comfortable and largely as advertisedHost:
carol is helpful prior to arrivalthe owner remained in touch throughout and was very responsive and helpfulthe owner was extremely helpful in providing information for our arrival and staythe owner was wonderful to work with from pre-reservation through the end of our staythe host is very responsive and kind and you couldn't ask for a better retreatRead more reviewsLocation:
close to great hiking trailsand stores close by for easy accessthe house and location were both very picturesquethe location with proximity to lenox and west stockbridge and to many many local hikes was excellentperfect location great neighborhood access to the water for kayaking boating etc
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.
Top guest reviews
Amenities & Room:
the deck off the loft is nice with room to comfortably sit 2we loved the breakfast sandwiches and pizza from sherwood shoppethe house was clean comfortable in a quiet relaxing setting with stunning views onto a small lakewe played games on the kitchen table as well as used the screened in porch and deck tablethe house was cozy on a quiet picturesque lakeCleanliness:
the house was very clean and cozyit was clean peaceful and quietthe cabin was very clean and we thought the inside was actually nicer than it looks onlinethe house was very cute clean and the setting beautiful and peacefulthe cabin was clean and very comfortable and justin was extremely easy to work withHost:
the owner was very responsive and helpfuli can only say to the owner thank you sooo muchjustin was very responsive and helpfuljustin was very quick with responses leading up to our stay and helpful with the fireplaceowner is very responsive and house had everything you need and then someRead more reviewsLocation:
location was good for area hiking and activitiesfun location and as others have said must be incredible in the summergreat waterfront location with a dock which we fished off of all weekend and actually caught several fishwe skied at otis ridge and loved the short walk to the sherwood shoppe for dinnerthat tells you something right there gorgeous house right on the water beautiful yard and location
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.
Top guest reviews
Amenities & Room:
comfortable beds in alcoves including a twin bed up a small laddergood wifi access and tv with raku with many channels including prime and netflixa/c worked great on one really hot night and others the fans were all that was neededkitchen set up for light cooking augmented by outdoor grill perfect for usthe beds are very comfortable the deck terrific for meals and the lakefront peaceful and invitingCleanliness:
the room was very clean and it had everything we neededvery clean and wonderful hoststhe loft had everything we needed and was clean and cozythe lake is gorgeous and so clean and clearthe loft is rustic but very cleanHost:
our hosts were friendly and helpfultim and gail are gracious hostsgail and tim were wonderful hostsgail & tim were wonderful and truly exceptional hoststhe hosts were extremely friendly and accommodatingRead more reviewsLocation:
appalachian trail near by a bonus perfect location and hostsit might be good to make its location clearergreat location close to many wonderful museums and hiking opportunitiesthe loft did not disappoint the location is greatbeautiful setting and close to several small towns and places to visit
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.
Top guest reviews
Cleanliness:
it was impeccably clean with soft comfortable linensthe place is super clean and well equippedplace was spotless dogs had room to run around outside and play in the lakehouse is super cute and clean and owners responsive to little snafu with immediate resolutionthe location was excellent and the home itself was very clean and welcomingHost:
host was great-very accommodating and responsive to questionslarry was extremely accommodating and very responsive to any questions about the home or the areaa big thank you to the owner for sharing it with usowner provided a detailed and thorough overview which made the check in and acclimation process simple and easylarry was very helpfulRead more reviewsLocation:
great location house was greatlocation was fantastic close to the outlets and not too far from ski butternutthe towns that are close are greatgreat place for a fall trip
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.
Top guest reviews
Amenities & Room:
the deck furniture was superbly comfortable and allowed for reading lounging and gazing at the waterthe kitchen is nice and large and the master bedroom is very comfortable and lots of closets throughoutthe bed was extremely comfortableCleanliness:
it was amazingly clean and updatedvery clean very cozy very privatevery comfortable very clean and very lovelythe house is so comfortable and cleanthe cottage is cozy clean and comfortableHost:
the owner was kind and very responsivecalled my contact and she was helpfulthe owner was great and communication was prompt and easyexcellent communication with the host before our stay and a thoughtful welcome gift waiting for usRead more reviewsLocation:
great barrington was fun and so closenearby downtown great barrington was fun with lots of cute restaurants and shopswhat an adorable cabin on a perfect locationloved it so relaxing and close to great barringtona+++ it was a fantastic location for our yearly ice fishing weekend
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.
Top guest reviews
Amenities & Room:
great place with great views comfortable and spaciouswould appreciate 2 more dining room chairsthe rooms we all very spacious and the balcony off the master bedroom was a favorite spotonly suggestion is some additional seating and lighting in the living room thank youthe dining room-into-sitting room looking over the lake is breathtakingCleanliness:
everything is clean and newvery clean well maintainedclean great for larger groupsit is always perfectly cleaned and well stocked with toilet paper cleaning supplies etcthis was a very nice clean propertyHost:
communication was always quick helpful and kindRead more reviewsLocation:
great location and house was perfectbeautiful house well stocked great locationhouse 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
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.
Top guest reviews
Amenities & Room:
beautiful views from the upstairs sun room & from the downstairs covered deckthe view from the front room were breathtakingthe kitchen was well equipped and all the furnishings very very nicekitchen well equipped & weber grill worked greatthe view was gorgeous and the weather warm enough for us to enjoy the beautiful sun roomCleanliness:
it was very clean and well organizedclean comfortable and nice decorthe house was clean everything workedgreat house clean & comfortablethe house was sparkling clean and well equippedHost:
the owner is pleasant and very helpfulowner was helpful and responsivei thank the owner for sharing his home away from home with usthe owner went out of his way to ensure that our stay was most pleasantbob was also very responsive during our stayRead more reviewsLocation:
the location is terrificthe location was convenient and beautifulperfect location for our time spent visiting family and friendsgreat location on a small peninsula on a large lakegreat location convenient to lenox/tanglewood
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.
Top guest reviews
Amenities & Room:
we especially loved the light-filled rooms lake views and super-cleanliness of rooms furnishings and kitchen supplieseasy access to the lake and there was plenty of room for our two familiesCleanliness:
the house was extremely clean and very spacious for usthe house was modern well equipped and extremely clean and well cared forHost:
jon was a great hostjon was a helpful and accessible hostowner is very easy to communicate withowner jon was very responsive and super helpfuljon the owner was excellent to deal withRead more reviewsLocation:
the location is beautiful the house very cleanthe location on the water was beautiful and we enjoyed the kayaks and canoe every eveningquiet and peaceful area
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.
Top guest reviews
Cleanliness:
nice clean lots of bedsthe house was clean and well equippedclean spacious and convenient couldn’t ask for morehouse was very clean and open and airy with plenty of group for out group of 8Host:
host is super responsive and friendlywe had a lovely stay and dori our host was wonderful perfect place for a large groupthe beach area was perfect for the kids the house had plenty of room and very kid friendlyRead more reviewsLocation:
excellent location and excellent ownersthe location is perfect for a family reuniongreat location - easy to ski at butternut and nearby lee a great destination for restaurantsthe location was a the perfect peaceful escape from the city
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.
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