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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Sandisfield Vacation Homes

Spacious Home nestled along the Blackberry River in Northwest CT
Enjoy cooking and dining in this well-equipped kitchen with a central island, appliances, and a dining area that opens to a deck with a grill.

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"The team stayed here for a curling tournament. Great location for that and perfect for 4 non-couple guests"
Spacious Home nestled along the Blackberry River in Northwest CT
Peace and quiet on the lake
Enjoy the airy feel of this room with a high ceiling and skylight, featuring a balcony with a railing.

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
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Enjoy meals in this elegant dining area with a central table and six chairs, surrounded by high ceilings and large windows.

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

10.0 out of 10, Exceptional, (127)
"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
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Escape to a serene lakeside retreat surrounded by lush greenery and vibrant flowers.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Deluxe Queen Room with 2 Queen Beds
Guest rooms lead to a covered walkway with a tiled floor.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (3)
"Pool is caving in with pool cover partly pulled away. Gate to access pool area was unlocked. Hazard for children. Staff is not onsite. Room was clean, but sheets had stains. Used bar of soap left on bathroom sink. "
The price is CA $136
CA $183 total
includes taxes & fees
Sep 1 - Sep 2
Deluxe Queen Room with 2 Queen Beds
Big farmhouse in the foothills of the Berkshires
Surrounded by lush greenery, this serene property features a beautifully maintained front yard with flowering shrubs and a neatly trimmed lawn.

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is CA $275
CA $499 total
includes taxes & fees
Aug 11 - Aug 12
Big farmhouse in the foothills of the Berkshires
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the surrounding landscape.

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 CA $358
CA $625 total
includes taxes & fees
Aug 10 - Aug 11
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Terrace/patio

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

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Lake Congamond Cozy Stylish Comfortable House
Enjoy a serene lakeside retreat with a boat dock and tranquil views.

Lake Congamond Cozy Stylish Comfortable House

2.0 star property
10.0 out of 10, Exceptional, (4)
"This cozy cottage was perfect. It was definitely a great lication and close to a lot of stores. The beds were really comfortable too. Thesellerr was super helpfula sn"
Lake Congamond Cozy Stylish Comfortable House
Spectacular views and close to Great Barrington.
Relax in this inviting living area with a high ceiling, brick fireplace, and expansive windows offering views of the surrounding landscape.

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay in Great Barrington for the long holiday weekend. The house is very comfortable, super clean, and the property is lovely. We were able to cool off in the pool and enjoy time with family. 10/10!"
Spectacular views and close to Great Barrington.
Relax or be active! The choice is yours in this pet-friendly family home.
Enjoy cooking in this well-equipped kitchen with a central island, stovetop, and ample counter space.

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

10.0 out of 10, Exceptional, (13)
"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.
Falls Reach In The Heart of Copake
Property grounds

Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake
Woodland A-Frame
Spacious living area with a high ceiling, stone accent wall, and kitchen island.

Woodland A-Frame

10.0 out of 10, Exceptional, (1)
"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
Poolside Luxe at Long Pond
Exterior

Poolside Luxe at Long Pond

Poolside Luxe at Long Pond
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Relax by the fire pit in a serene forest setting, surrounded by comfortable seating.

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

The price is CA $374
CA $688 total
includes taxes & fees
Aug 31 - Sep 1
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining

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

10.0 out of 10, Exceptional, (5)
"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
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel range hood, and large window offering a view of the outdoors.

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!
Quiet Cabin On Over 12 Acres Of Woods!
Cozy living space with a central island kitchen, spiral staircase, and comfortable seating area.

Quiet Cabin On Over 12 Acres Of Woods!

10.0 out of 10, Exceptional, (11)
"The property was perfect for our weekend in Becket. The house was very comfortable and the grounds quite beautiful. We enjoyed our visit."
Quiet Cabin On Over 12 Acres Of Woods!
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
TV, table tennis, books

8 Mi to Tanglewood & Butternut Ski: Spacious Home!

10.0 out of 10, Exceptional, (1)
"This place truly has everything you could want in a vacation rental. It was exceptionally clean, spacious, and accommodating. From the moment we arrived, it felt like a home away from home. The host clearly puts a lot of care into maintaining the property and ensuring guests are comfortable. We had everything we needed for an enjoyable stay. Highly recommend and would definitely book again!"
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Relax in this serene space with a comfortable chair and a staircase leading to an upper level.

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (45)
"The home is very nice and cozy. It really felt like a comfy home."
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Reallt liked the property. Great location. Would suggest more comfortable chairs outside."
Susan 6-night trip
Posted 15 hours ago
Berkshire Mountain Lodge