Vacation rentals in The Berkshires

4.97 out of 5 average rating, 395 reviews

Cabin in Bovina Center

Delightful Cabin with Extras

SarahRating, 5 stars1 month ago

Had a lovely long weekend at Pamela & Alan's warm, cozy home. We made good use of the wood stove, grill, and hot tub and took advantage of the board game and DVD selections as well! We also enjoyed the local attractions such as the Putt Putt Van Winkle mini golf course, Brushland Eating House and Bovina Farm & Fermentory for delicious dinners, Wayside Cider, and even went for a little hike nearby. The house was clean and comfy and we felt right at home - thanks to Pamela and Alan for the wonderful stay!

4.98 out of 5 average rating, 128 reviews

Home in Lake Luzerne

River Cottage

JensyRating, 5 stars5 months ago

Brianna is a wonderful host, very friendly, always available and ready to help in anything we may need. The house is like a Dream House. Lovely living room with a fireplace, TV and a big and comfy sofa. Every room in the house was excellently decorated with a high test and good sense of space making you feel warm and welcome, like your own home. The surroundings are so beautiful that you even have a river running in the backyard. Like fairytale stories. The most amazing thing is the Kitchen fully equipped with seasonings, coffee, tea and beautiful crockery and pot sets. Everything you may need for a memorable vacation is here! We loved this place and definitely we're going to come back. Thank you very much Brianna, you're amazing!

5 out of 5 average rating, 51 reviews

Home in Hadley

The Summit on The Sacandaga is sure to Satisfy.

DebraRating, 5 stars1 week ago

great house with everything needed to enjoy the beautiful surroundings for a family vacation- pups included. the summit at sacandaga was everything we hoped for: beautiful lake views surrounded by mountains in a very private setting. the entire house was very clean and well appointed especially in bedrooms, kitchen and bathrooms. we loved our stay. heather was very responsive and helpful and we had no issues from start to finish- only a positive experience. we would definitely stay there again and highly recommend this beautiful spot on the lake.

4.96 out of 5 average rating, 25 reviews

Home in Old Chatham

Post and Beam Hilltop Sanctuary

CatherineRating, 5 stars3 months ago

We really enjoyed our stay at Sandi’s place. Each bedroom has its own bathroom, which is great for couples and families. The kitchen had everything we needed to cook a big NYE dinner. And it was just a few mins from Chatham center and I90, while still quiet and isolated. Sandi was great at communicating with us and was very flexible about check in and check out times, which we appreciated. We had one toddler with us and there was also a pack and play and a high chair. We would stay here again!

4.96 out of 5 average rating, 26 reviews

Cottage in Glen Spey

Lakeside Cabin

AndrewRating, 5 stars9 months ago

We had a perfect long weekend at Steven's cottage. It is bigger than it looks in the photos and was immaculately clean when we arrived. Steven was extremely responsive to all our questions and needs. The place is incredibly peaceful, a 2 min walk from the lake, on a private road where Steven owns all three houses. It was so relaxing and rejuvenating to spend time at this oasis with my partner and our best friends. There's a lot to love, but the best part is that the house comes with a private deck and dock, and unlimited access to various boats, to make your lake weekend whatever you want it to be. We loved that we could take our dogs to play fetch off the dock and not worry about getting in anyone's way or having to share any space. It was a great stay and we hope to go back!

4.94 out of 5 average rating, 243 reviews

Home in Northville

OnTheRiver/Adk decor, full kitchen, 2 bedrooms

KerryRating, 5 stars5 months ago

What a beautiful, warm and cozy space to spend a relaxing weekend! The view was perfect and the thoughtful touches throughout the home were appreciated. Beds were very comfortable! Thank you so much, we would love to return.

4.91 out of 5 average rating, 134 reviews

Apartment in Wilmington

Globetrotter Retreat too - Minutes to the Mountain

XianlongRating, 5 stars4 weeks ago

Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.

4.91 out of 5 average rating, 117 reviews

Home in Sheffield

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

FeliciaRating, 5 stars2 months ago

Sally responded to questions right away. She was really attentive - making sure snow was cleared and ice salted so that we could leave early in the morning after a big snow storm. The place was really conveniently located 15 minutes from ski Butternut. And it was immaculately clean and so cozy. It was a really nice stay.

4.9 out of 5 average rating, 129 reviews

Home in Middletown

Riverfront! Swim, Fish, Hot Tub & Game Barn.

SamanthaRating, 5 stars6 days ago

Beautiful home in a very private area. Lots of family games and lots of outside things todo. Me and my family had a wonderful Easter weekend get away. Only complaint I would have is the jacuzzi smelled weird and stuff was coming out of the jets but other than that it was perfect! We all were very comfortable and had a blast with the kids.

Vacation rentals for every style

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Kick off your hiking boots at these rustic lodgings

Popular amenities for The Berkshires vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in The Berkshires

5 out of 5 average rating, 9 reviews

Home in Bellows falls

Amazing Views, Skiing Nearby and Amenities Galore!

GillianRating, 5 stars2 months ago

We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!

4.95 out of 5 average rating, 39 reviews

Home in Saratoga Springs

Great Saratoga House with Pool Walk to Everything!

CaitrinRating, 5 stars4 months ago

Loved staying here! It was super cozy and a lovely home away from home for the holidays. House is as described and very spacious. Fireplace makes it extra cozy when the weather got cold. Host was very proactive and responded to any question or issue almost immediately. We will definitely be staying here again!

4.73 out of 5 average rating, 158 reviews

Chalet in Fleischmanns

Sauna equipped Belleayre Cozy Cabin

ChloeRating, 5 stars2 months ago

Perfect for a ski weekend. Sauna is great, and location cannot be beat.

4.87 out of 5 average rating, 15 reviews

Home in Monticello

Luxurious & Newly Renovated Catskills Lakehouse

ShelbyRating, 5 stars1 month ago

We had a weekend youth retreat and stayed at Alan’s spacious home. We had a great time together. the home was as described, the hosts were very friendly and accommodating, and everything was clean and in good condition. Would definitely recommend for a big group!

Tiny homes in Fort Edward

4.86 out of 5 average rating, 58 reviews

Tiny Home In Paradise “The Big Dipper”

AlannaRating, 5 stars9 months ago

If you’re looking for a quiet place to get away for the weekend, look no further!! Pete was so nice and incredibly responsive. My fiancée and I will definitely be staying here again!

4.79 out of 5 average rating, 19 reviews

Cottage in Hadley

The Great Sacandaga Cottage Experience

MatthewRating, 5 stars6 months ago

Such a cute classic cottage, we felt at home instantly. It is close to the mountains, hiking and the beautiful lake. It was a very short drive to tourist attractions and restaurants in Lake George.

4.93 out of 5 average rating, 42 reviews

Home in Westbrook

Private vacation home, close to beach

JaniceRating, 5 stars6 months ago

We loved our stay in Westbrook! Mia's lovely home exceeded our expectations in terms of decor, furnishings, cleanliness, comfortable beds, and well-stocked kitchen and bath ... all in a quiet and private setting. The house was especially well-situated for us. We had tickets for a special theater performance at Gillette Castle one evening, and then had to be in New Haven on the next day. All were easy drives. And, there are amazing fine dining options nearby. We'll definitely try to book this wonderful place any time we have events in the area. Thank you, Mia, for a magical Autumn weekend in Connecticut!