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Check prices for these dates

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

Browse Select Sheffield 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
Charming cottage with lake access, wood burning fire place, and WiFi
Relax in this inviting living room with a sofa, dresser, and small table.

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
9.0 out of 10, Wonderful, (7)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
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
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
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.
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Relax on the deck surrounded by trees, with Adirondack chairs and a small table for a peaceful retreat.

Taconic Hideaway – Swimming, BBQ Pit, Hiking

2.0 star property
10.0 out of 10, Exceptional, (6)
"Great stay. The host was great with communicating directions and details for the home and even shared local recommendations. We appreciated their quick response to our questions, too. "
Taconic Hideaway – Swimming, BBQ Pit, Hiking
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
Stylish Pine Plains Home Near Parks & Hiking!
Enjoy cooking in this fully equipped kitchen with a range, oven, microwave, and sink.

Stylish Pine Plains Home Near Parks & Hiking!

9.8 out of 10, Exceptional, (15)
"Place looked great in pictures and turned out to be even better! Will definitely stay there again."
Stylish Pine Plains Home Near Parks & Hiking!
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
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, (12)
"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!
Cabin Retreat in the Berkshire Woods
Cozy living area with a central staircase, comfortable seating, and dining space.

Cabin Retreat in the Berkshire Woods

Cabin Retreat in the Berkshire Woods
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
Relax in a spacious living area with a high ceiling and comfortable seating, perfect for socializing and unwinding.

Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

10.0 out of 10, Exceptional, (94)
"Exactly what you want in a ski house!"
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
Cottage at Copake Lake
Situated in a wooded area, this cabin offers a natural and serene environment with a porch and a fire pit for relaxation.

Cottage at Copake Lake

10.0 out of 10, Exceptional, (64)
"We had great relaxing stay. The host was very responsive to any questions i had"
Cottage at Copake Lake
Secluded Family Home in Serene Stockbridge Woods
Enjoy meals with family and friends in this spacious dining area with a long table and comfortable seating for four.

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (21)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods
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 Sheffield Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"I like that it is clean, quiet and convenient. The staff is very nice and helpful."
Ellen 1-night trip
Posted 1 day ago
Quality Inn