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Compare 88 Cottages in Sheffield with updated reviews, rates, and availability.

Perfect Vacation Get Away - Historical New Marlborough
Exterior
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is SAR 563
SAR 1,015 total
includes taxes & fees
25 Jun - 26 Jun
Perfect Vacation Get Away - Historical New Marlborough
Private Island - Largest Fresh Water Reservoir in Mass....
Aerial view
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
The Blue Elm - A Historic Berkshire Cottage
Exterior
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (2)
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
The price is SAR 938
SAR 1,789 total
includes taxes & fees
24 Jun - 25 Jun
The Blue Elm - A Historic Berkshire Cottage
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East Otis Vacation Rental w/ Private Deck & BBQ!
East Otis Vacation Rental | Studio | 1BA | 800 Sq Ft | Steps to Enter
East Otis Vacation Rental w/ Private Deck & BBQ!
9.6 out of 10, Exceptional, (7)
"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!
Idillic summer getaway in Litchfield Hills, CT.
Property grounds
Idillic summer getaway in Litchfield Hills, CT.
10.0 out of 10, Exceptional, (11)
"Came here for a birthday getaway filled with hiking, and great restaurants! It rained the entire time, but this beautiful cottage was so relaxing, with the windows overlooking the private backyard, we simply sat and read and watched the rain roll by. Lots of room, spacious bedrooms. Great for a family."
Idillic summer getaway in Litchfield Hills, CT.
Sunny Lakeside Artist's Cottage with Dock and Kayaks
Property grounds
Sunny Lakeside Artist's Cottage with Dock and Kayaks
Sunny Lakeside Artist's Cottage with Dock and Kayaks
Cozy cottage with kettle pond lake 2 minutes away
Exterior
Cozy cottage with kettle pond lake 2 minutes away
Cozy cottage with kettle pond lake 2 minutes away
Country Cottage Retreat
Property grounds
Country Cottage Retreat
10.0 out of 10, Exceptional, (9)
"we had a wonderful time! the cottage was very comfortable and really well-appointed. We made the most of the fireplace and our two dogs loved the access to the field and woods nearby. Susanne, the host, gave us great directions and was super friendly and helpful and we really appreciated the scones,chocolate and fresh local eggs left for us. We made the most of the easy access to the Rhinebeck restaurtants and hikes in the area and would love to come back! Thank you"
Country Cottage Retreat
Two Bedroom Cottage Close To Town
Exterior
Two Bedroom Cottage Close To Town
9.2 out of 10, Wonderful, (12)
"Beautiful location and property. Close to hiking and dining. House is perfect and has everything you need."
Two Bedroom Cottage Close To Town
Quiet rustic cottage with shared lake access
Quiet rustic cottage with shared lake access
10.0 out of 10, Exceptional, (94)
"A very nice stay. Communication with the host was great. We kept bothering her with questions and she responded quickly. The place is really beautiful. We lit a fire each night and played some of the provided games and watched Netflix. It's an easy drive to Great Barrington to get groceries at the Berkshire coop. We also took advantage of our surroundings and hikes on the AT a little each day. Next time we'll use the host's canoe to explore Lake Buel. The only minor complaint I would have is...
Quiet rustic cottage with shared lake access
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Main deck
The Cottage at Highland Lake, year-round, waterfront with a boat dock
10.0 out of 10, Exceptional, (3)
"happen to get beautiful weather while staying at the cottage at highland lake. so nice to wake up with a view, and then at sunset to enjoy the glass like water."
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Fun Getaway Lakehouse in the Hudson Valley
Tiny house for glamping! Sleeps 2 and fire pit!
Fun Getaway Lakehouse in the Hudson Valley
10.0 out of 10, Exceptional, (8)
"This was an excellent stay in a perfect location to explore both the Hudson Valley and the Berkshires. Host communicated seamlessly, and house is precisely as described. Very spacious and furnished in a neutral tones, minimalist style. Would recommend."
Fun Getaway Lakehouse in the Hudson Valley
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Monterey Vacation Rental | 3BR | 1BA | 900 Sq Ft | Stairs Required
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
10.0 out of 10, Exceptional, (2)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Cottage Retreat - Historic Cottage Home w Home Gym
This bedroom comes with a king-size bed that is perfect for your stay.
Cottage Retreat - Historic Cottage Home w Home Gym
6.0 out of 10, (3)
"Door code invalid as relayed. Check in time not honored. Upon entry thermostat read 41degrees on a a damp cold day. Multiple diffusers, plug-ins did not offset the dirty diaper, blood stained sheet, & foul bathroom smell. Meager linen supply, lack of detergent, rodent bags rounded out this thoroughly unpleasant experience."
Cottage Retreat - Historic Cottage Home w Home Gym
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Relax on the large deck with lake views
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
10.0 out of 10, Exceptional, (2)
"The house is very cozy with a well appointed kitchen and a beautiful view of the lake. We would like to go back some day. The host is very responsive and kind."
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Peaceful Goshen Cottage w/ Screened Porch & Views!
Goshen Vacation Rental | 3BR | 1.5BA | 1,500 Sq Ft | Stairs Required for Entry
Peaceful Goshen Cottage w/ Screened Porch & Views!
9.0 out of 10, Wonderful, (27)
"House was just right for our needs . Very comfortable ,clean, and private. We were in the area for family weekend at Kent School, wish we had more time to spend at the home and enjoy the great outdoors with the fall foliage and the nice outdoor fireplace. would definitely stay here again.."
Peaceful Goshen Cottage w/ Screened Porch & Views!
Cozy Berkshires Cottage w/ 11 Private Acres!
Lee Vacation Rental | 1BR | 1BA | 1,300 Sq Ft | Steps Required
Cozy Berkshires Cottage w/ 11 Private Acres!
Cozy Berkshires Cottage w/ 11 Private Acres!
Creekside Cottage The Fitz House Red Hook NY
Living area
Creekside Cottage The Fitz House Red Hook NY
10.0 out of 10, Exceptional, (2)
"A quiet stay in a cozy cottage. Smaller than it looks but perfect size for a couple for the weekend."
Creekside Cottage The Fitz House Red Hook NY
Beachwood Cottage
Property grounds
Beachwood Cottage
10.0 out of 10, Exceptional, (1)
"Second time staying at the property. Comfortable, low key cabin. Access to private beach a big plus. Near Lenox, Stockbridge and Tanglewood."
The price is SAR 1,032
SAR 2,028 total
includes taxes & fees
8 Jul - 9 Jul
Beachwood Cottage
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Property grounds
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.5 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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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.

Other property types in Sheffield

Cheerful 3-bedroom cottage with woodstove
great kitchen for cooking in
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (22)
"This home was "as advertised" - plenty of room. Nice neighborhood setting. Well stocked kitchen & nice outside area in the backyard / deck. We used it as a base camp for section hiking the appalachian trail."
The price is SAR 840
SAR 1,831 total
includes taxes & fees
27 Jun - 28 Jun
Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (80)
"We have 20 years experience renting homes for family gatherings and this is the most interesting and amazing property. Gardens galore, plenty of space to congregate or go off by yourself, fully appointed kitchen, and comfortable space. We were a party of ten and everyone loved the experience."
Antique Farmhouse Totally Restored
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
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.

Recent reviews of Sheffield hotels
Expedia verified reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"Loved the lake in the back !!!"
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 2 days ago
The Black Swan Lee - Lenox, Ascend Hotel Collection