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Check prices for these dates

Next weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Sheffield Cottages

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Relax on a deck overlooking a serene body of water surrounded by lush greenery and trees.

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2.0 star property
9.0 out of 10, Wonderful, (4)
"Cozy, serene and bucolic waterfront hideaway within driving distance of Tanglewood, Shakespeare & Company, Jacob's Pillow and all the wonderful food and cultural Berkshire gems! Julie and Russ were amazing hosts. Great communication and wonderful restaurant and museum suggestions. Definitely planning another long weekend retreat!"
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Private Island - Largest Fresh Water Reservoir in Mass....
Relax by the fire pit in this serene outdoor seating area overlooking the water.

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....
Idillic summer getaway in Litchfield Hills, CT.
Situated in a serene park-like setting, this house features a two-story facade and a garage, surrounded by a stone wall and a winter landscape.

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"Great spot close to Limerock Raceway - private, cute, and a perfect spot to stay! The owners are so nice and accommodating - I couldn’t say nicer things about this place and will be back!"
Idillic summer getaway in Litchfield Hills, CT.
Summer Lake Cottage, private beach, Berkshire Hills, small village
Escape to a serene lakeside retreat surrounded by trees and a tranquil atmosphere.

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (81)
"Amazing cabin, thank you for a beautiful stay! We came in for a wedding and this was a great location to where the wedding was held. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Cozy cabin surrounded by lush greenery, featuring a rustic exterior and a spacious garage.

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (40)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
East Otis Vacation Rental w/ Private Deck & BBQ!
Escape to a secluded cabin surrounded by mature trees, featuring a cozy porch and deck with seating area.

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (10)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
Two Bedroom Cottage Close To Town
Surrounded by mature trees, this single-story house offers a serene environment and a covered outdoor area.

Two Bedroom Cottage Close To Town

9.2 out of 10, Wonderful, (23)
"We enjoyed three nights at the cottage. It's beautifully decorated, comfortable, warm and welcoming - a perfect home base for nearby hikes and exploring the area. The large yard was perfect for playing soccer with our child. Renters note: we also had a fabulous meal at nearby restaurant Fern. "
Two Bedroom Cottage Close To Town
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Enjoy a serene outdoor space with a table, two chairs, and a rocking chair, overlooking a tranquil body of water surrounded by trees.

Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake

10.0 out of 10, Exceptional, (7)
"Very clean, cute house right on the lake. We enjoyed our time there. "
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
House (2 Bedrooms) | Interior

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Creekside Cottage The Fitz House Red Hook NY
Cozy cabin surrounded by trees, featuring a small porch with two chairs and a table.

Creekside Cottage The Fitz House Red Hook NY

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay. Communication with host was excellent. Highly recommend the location for a couple."
Creekside Cottage The Fitz House Red Hook NY
The Blue Elm - A Historic Berkshire Cottage
Enjoy outdoor dining or relaxation on the porch, surrounded by a serene lawn and mature trees.

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (8)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is CA $275
CA $566 total
includes taxes & fees
Aug 10 - Aug 11
The Blue Elm - A Historic Berkshire Cottage
Beachwood Cottage
Stroll through the serene garden, surrounded by lush trees and shrubs, and discover a tranquil atmosphere perfect for relaxation.

Beachwood Cottage

9.6 out of 10, Exceptional, (5)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage
Quiet rustic cottage with shared lake access
Set amidst a serene natural setting, this home features a stone chimney, large windows, and a two-car garage.

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (109)
"Lovely lake house at the end of a long private road, perfect for a quiet getaway, close to all kinds of hiking and other natural attractions. Our hosts were super friendly and responsive. Highly recommended."
Quiet rustic cottage with shared lake access
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Surrounded by lush greenery, this two-story house offers a welcoming outdoor space with a deck and porch.

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.4 out of 10, Exceptional, (13)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Enjoy a serene lakeside view from this deck overlooking a calm body of water.

The Cottage at Highland Lake, year-round, waterfront with a boat dock

10.0 out of 10, Exceptional, (6)
"Really enjoyed this cute little cottage right on the lake. Brought our 3 year old to visit family. Nice bedrooms. Gorgeous deck. Really good communication from the owner as far as directions and such. Would go back for sure. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Grandparent’s Cottage 250 steps to the lake
Sun loungers, beach towels

Grandparent’s Cottage 250 steps to the lake

Grandparent’s Cottage 250 steps to the lake
Perfect Vacation Get Away - Historical New Marlborough
Cozy cabin with a small porch and Adirondack chairs, surrounded by lush greenery.

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (55)
"Lovely place!"
The price is CA $206
CA $380 total
includes taxes & fees
Sep 3 - Sep 4
Perfect Vacation Get Away - Historical New Marlborough
A-frame Cabin w/ Furnished Deck in Becket!
House (2 Bedrooms) | Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Private Hot Tub: Hudson Valley Cabin Retreat!
House (3 Bedrooms) | Interior

Private Hot Tub: Hudson Valley Cabin Retreat!

3.0 star property
Private Hot Tub: Hudson Valley Cabin Retreat!
Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia
Surrounded by lush greenery, this single-story house offers a serene and setting with a cozy porch and seating area.

Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia

10.0 out of 10, Exceptional, (1)
"This was the perfect size cottage for 5 of us, with two rooms with queen size beds and one small room with a twin. The setting was very pretty, and the salt water heated pool was a good size and my grandchildren enjoyed swimming in it. We were within walking distance of the small town, and I would recommend staying there."
Charming 3bdr Magnolia cottage with heated saltwater pool, AC and WiFi in Amenia
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Nice place, well maintained, friendly staff, excellent breakfast. Good location but on a main road in a commercial area. Very convenient and comfortable!"
Jesse 2-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham