Search Sheffield Cottages

Compare 86 Cottages in Sheffield with updated reviews, rates, and availability.

Private Island - Largest Fresh Water Reservoir in Mass....
Property grounds
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....
Perfect Vacation Get Away - Historical New Marlborough
Property grounds
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 $150
$272 total
includes taxes & fees
Jun 24 - Jun 25
Perfect Vacation Get Away - Historical New Marlborough
Cozy cottage with kettle pond lake 2 minutes away
View from property
Cozy cottage with kettle pond lake 2 minutes away
Cozy cottage with kettle pond lake 2 minutes away
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Idillic summer getaway in Litchfield Hills, CT.
Exterior
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.
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 $200
$413 total
includes taxes & fees
Jun 16 - Jun 17
The Blue Elm - A Historic Berkshire Cottage
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
Fridge, microwave, oven, stovetop
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
Fridge, microwave, oven, stovetop
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
Beach nearby, sun loungers, beach towels
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
Property grounds
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
Dining
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
Interior
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!
Property grounds
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!
Fridge, microwave, stovetop, dishwasher
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!
Exterior
Cozy Berkshires Cottage w/ 11 Private Acres!
Cozy Berkshires Cottage w/ 11 Private Acres!
Creekside Cottage The Fitz House Red Hook NY
Sport court
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 $275
$543 total
includes taxes & fees
Jul 8 - Jul 9
Beachwood Cottage
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Interior
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.5 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Summer Cottage on 5-acre woods w Games & BBQ, 20 min to Hudson
Smart TV, fireplace, books
Summer Cottage on 5-acre woods w Games & BBQ, 20 min to Hudson
10.0 out of 10, Exceptional, (1)
"Absolutely beautiful location. Lots of hiking nearby. Countless places, towns, attractions, etc. to check out. The house was better than the pictures suggest. We are already making plans to return in the Spring / Summer."
Summer Cottage on 5-acre woods w Games & BBQ, 20 min to Hudson
Beautiful Berkshires Cottage on Lake Buel
Interior
Beautiful Berkshires Cottage on Lake Buel
10.0 out of 10, Exceptional, (1)
"I’ve been visiting the Berkshires for decades and never stayed at a place with such an amazing view of Lake Buel! Sunrise right from my bed. The house was stocked with everything that was needed for an amazing weekend. Wonderful place to stay!"
Beautiful Berkshires Cottage on Lake Buel
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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
Property grounds
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 $217
$479 total
includes taxes & fees
Jun 19 - Jun 20
Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
Exterior
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
Interior
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.

Sheffield Cottages information

Number of reviews
213
Accommodation
86 Cottages
Lowest Price
$150
Highest Price
$275

Frequently asked questions

How much do cottages in Sheffield cost?
Expect to pay between $150 and $275 per night for cottages in Sheffield. Whatever your budget, a wonderful stay is a click away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Sheffield?
There are 86 cottages in Sheffield. No matter if you’re taking a trip with the kids or planning a getaway with your pals, Expedia can help you find the right place to enjoy nature’s beauty.
Why book your cottage in Sheffield with Expedia?
We think a getaway should be easy, so if you’re chasing cottages in Sheffield at a competitive price, Expedia has you covered. Keep costs down and check in to an economical option far from the hustle and bustle, or book a luxury cottage to treat your loved ones.
How can I find cheap cottages in Sheffield?
With Expedia’s user-friendly filter tool, comparing cheap cottages in Sheffield is a snap. To find properties that are very pocket friendly, narrow down your search by amenities, budget and star rating.
What is there to do in Sheffield near my cottage?
There are lots of superb things to see and do in Sheffield. Discover well-known attractions like Ski Butternut, Bash Bish Falls State Park and Mahaiwe Performing Arts Center. Umpachene Falls Park, Mount Everett State Reservation and Les Trois Emme Winery are other must-see’s.

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
"We are just stopping overnight, and feel we got lucky. This is a lovely small hotel on a lake with great views, boats to rent, and an excellent restaurant. It would be great for a vacation. "
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