
Vacation rentals in Sandisfield
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Top-rated vacation rentals in Sandisfield
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Superhost

Cabin in New Marlborough
5 out of 5 average rating, 3 reviewsCosmo Cabin: Your Cozy Escape
DavidRating, 5 stars1 month ago
We absolutely loved our stay at this cozy, charming cabin! It’s the perfect place to unplug and unwind. Nestled in a peaceful, quiet setting, the cabin feels like a true retreat from everyday life. We especially enjoyed the screened-in porch for morning coffee and evening chats. The nearby waterfalls (a 30–40 minute walk or 10-minute drive) were a wonderful way to enjoy the area’s natural beauty. The two-person soaking tub was a highlight—so relaxing after a hike! The cabin is thoughtfully equipped with a small but functional kitchen, which made it easy to prepare simple meals. We also appreciated the high-quality linens and comfortable bed—such a nice touch that made our stay feel special. While it’s ideal for unplugging, there is Wi-Fi if you need it. There are also some cute towns nearby, full of antique shops and local charm. It was the perfect blend of nature, comfort, and low-key exploration. We’re already dreaming of our next visit!
Top guest favorite

Home in Sandisfield
5 out of 5 average rating, 33 reviewsWaterfront oasis in heart of Berkshires
LisaRating, 5 stars5 days ago
The location was peaceful and beautiful with great local restaurants, farms, and hiking. The reservoir was a nice amenity with the kayaks and canoe. The house was well maintained and comfortable with pretty views on the first floor. We enjoyed our stay
Guest favorite

Apartment in Winsted
4.93 out of 5 average rating, 89 reviewsGetaway for a weekend! Close to Ski Sundown.
KimberlyRating, 5 stars1 week ago
Great stay, convenient location. Lots of food options in surrounding area. We enjoyed our stay very much.
Guest favorite

Tiny home in New Hartford
4.91 out of 5 average rating, 53 reviewsWest Hill Outpost
JessicaRating, 5 stars2 weeks ago
My boyfriend and I really enjoyed our stay. Everything was exactly like in the photos. It felt very clean and new for also staying in a quiet rural area. Michael was very communicative and helpful— even down to warning about some potholes on the road! It was a great relaxing getaway from the city and we enjoyed the house and area very much. For such a small space it had everything you could need and more.
Guest favorite

Barn in Monterey
5 out of 5 average rating, 19 reviewsA Writer's Retreat at The Barn
AngelaRating, 5 stars1 month ago
What a beautiful place to stay! Jaryn made it easy to check in, gave clear instructions, and offered any help we needed. As other reviewers noted, if you know you have limited access to cooking, you'll be fine. We maximized the fridge and microwave and used the coffeemaker each morning. The barn conversion is incredible - my husband is an architect and was very impressed. Our favorite was the screened-in porch, and we spent lots of time sipping coffee, writing, and enjoying meals out there (I brought my blanket!). Monterey is an incredible place to stay. Beautiful everywhere you go, but close to so much.
Guest favorite

Home in Tolland
4.95 out of 5 average rating, 60 reviewsSpacious Home w/ Hot Tub in Private Lake Community
NanditaRating, 5 stars2 weeks ago
Tina's house was immaculate, comfortable and cozy. We enjoyed the hot tub very much. Kids had a ball in the game room downstairs. Tina responded promptly to our requests. I would highly recommend her home for family get togethers.
Guest favorite

Home in New Marlborough
4.86 out of 5 average rating, 7 reviewsBiggest Tiny Birdwatcher's Paradise
JenniferRating, 5 stars2 months ago
We really enjoyed our long weekend at Jake’s rental. I love the aesthetic of the space. It was very comfortable for myself, my husband and our mini Aussie dog. It is a quick drive to Great Barrington. We loved Mooncloud which features interesting cocktails and charcuterie. Down the street from the house is access to the Appalachian Trail. It was an easy drive to Pittsfield for my brother’s birthday. Would love to come again!
Superhost

Home in Otis
4.9 out of 5 average rating, 52 reviewsBerkshire Lakefront Lighthouse Getaway
AdrienneRating, 5 stars3 weeks ago
We had a great time at Lee’s lighthouse! What a beautiful setting on the lake and a great neighbor hood!! Easy access to the water and we loved the outdoor shower. We will certainly be back for another stay!
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