Holiday Homes in Sandisfield

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Featured Holiday Homes in Sandisfield

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (70)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

10.0 out of 10, Exceptional, (58)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is AU$770
includes taxes & fees
28 Aug - 29 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (6)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (48)
"What a wonderful property for our girls trip! The house is clean, there’s so much hangout space, and it’s so well supplied. "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (128)
"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Relax or be active! The choice is yours in this pet-friendly family home.

9.8 out of 10, Exceptional, (14)
"Home was exactly as listed, very comfortable and convenient for my family’s trip. "
Relax or be active! The choice is yours in this pet-friendly family home.

Poolside Luxe at Long Pond

Poolside Luxe at Long Pond

Linny’s Lake Retreat, Family-Friendly & Dock Access

9.8 out of 10, Exceptional, (22)
"Amazing place and great hosts! This place was perfect for us to stay while in town visiting family. Will definitely be staying here again"
Linny’s Lake Retreat, Family-Friendly & Dock Access

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

10.0 out of 10, Exceptional, (1)
"Smooth and straightforward check-in process. They were accommodating to our schedule and communicated everything in a timely manner. House was clean and everything looked as listed. Kitchen was well stocked with up to date appliances and plenty of utensils which was a nice surprise. Plenty of space for 7 of us, would suggest bringing an air mattress though if with a larger party. Overwhelming positive experience overall. "
The price is AU$791
includes taxes & fees
26 Aug - 27 Aug
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "
The price is AU$787
includes taxes & fees
3 Sept - 4 Sept
Cheerful 3-bedroom cottage with woodstove

Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Woodland A-Frame

10.0 out of 10, Exceptional, (2)
"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "
Woodland A-Frame

Lakefront Bungalow

9.6 out of 10, Exceptional, (10)
"Nice location on water, clean, kitchen had all our needs--would stay there again."
Lakefront Bungalow

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (46)
"We went as a family to get away from the city life for the weekend. We have no complaints except that it could’ve been a bit cleaner in the sense that there were many cobwebs. Nonetheless we rlly enjoyed our weekend in Great Barrington "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (91)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (75)
"Perfect for a family vacation with a baby and dog. Particularly enjoyed having drinks and dinner on the deck, overlooking the water. Felt like a private retreat. "
Stay Lakeside This Summer!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sandisfield Hotel Reviews