Sheffield Vacation Rentals from ￥16,031: Search Short-Term Rentals

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Vacation Rentals in Sheffield

Relax by the clear pool surrounded by lounge chairs and lush greenery.

"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."

Stroll through the beautifully landscaped garden, surrounded by a variety of plants and flowers, to the entrance of this two-story house.

"Enjoyed the property, location and charming house that was well stocked with everything we needed."

Cozy cabin interior with a high ceiling and wooden beams, featuring a central dining table and fireplace.

"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "

￥118,197 total

includes taxes & fees

Jul 28 - Jul 29

Steps lead down to the tranquil lake's edge, surrounded by trees and a rustic stone wall.

"A good place for vacation that you can enjoy and rest. Very nice and safe place."

5 bedrooms, iron/ironing board, WiFi, bed sheets

￥126,658 total

includes taxes & fees

Aug 3 - Aug 4

Relax in this inviting living room with a sofa, dresser, and small table.

"Oriana was awesome and I look forward to staying there again."

Situated in a grassy yard, this charming house features a sloped roof, chimney, and a small window.

"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"

Relax in this serene room with a large bed, stone fireplace, and forest views.

"We had a wonderful stay. The cabin was clean and comfortable! "

Experience the perfect blend of traditional and contemporary style in this inviting space, featuring a plush sofa, wooden coffee table, and modern kitchen.

"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"

Guest rooms lead to a covered walkway with a tiled floor.

"The chemical smell in the room was overwhelming. There was no personal contact We called the number provided and was told We would get a full refund."

￥21,192 total

includes taxes & fees

Aug 10 - Aug 11

Stately two-story house with a central columned entrance and white balustrade.

"Loved the property. Perfect for our gathering."

Relax in a serene outdoor space with Adirondack chairs and a shaded gazebo.

"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "

Relax by the pool surrounded by lush greenery and a shaded patio area.

"Quiet, private , comfortable and clean sanctuary! Highly recommend…!! "

Relax on the lakeside dock with Adirondack chairs and enjoy the serene view.

"Nice location on water, clean, kitchen had all our needs--would stay there again."

Enjoy the airy feel of this room with a high ceiling and skylight, featuring a balcony with a railing.

"I love this place! It's been beautifully remodeled and is very comfortable. I would love to visit when it's warmer, but it's very cozy in the snow. I can't wait to come back with my kids. "

Enjoy cooking in this well-equipped kitchen with a central island, white cabinetry, and a stainless steel range hood.

"Beautiful, spacious house in a great location!"

Enjoy cooking in this well-equipped kitchen with a central island, oven, and ample workspace.

"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."

Enjoy al fresco dining and socializing on this tranquil outdoor deck, complete with a barbecue grill and comfortable seating.

"We really enjoyed our stay here. Location was excellent. Very peaceful and quiet. The house was clean and had everything you needed. Would come again!"

￥58,317 total

includes taxes & fees

Jul 28 - Jul 29

Spacious interior with a high ceiling, central kitchen, and large windows.

"Great property for the fire and pool. Highly recommend for multiple families/couples. Close to town."

Surrounded by tall trees, this cozy cabin offers a peaceful retreat in a natural setting.

"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."

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Top Sheffield Hotel Reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

10/10 Excellent

"Everything was great."

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"We always stay here when we go to the Berkshires. Hot tub, pool and breakfast included. Great hiking trails and kayaking spots a short drive away. Barrington Brewery just across the street which is always a must for us!"

The Whitlock

10/10 Excellent

"I was in town to attend an inspection on a house we made an offer on in nearby Becket. The Whitlock was perfect for me. It was conveniently located, in town, close to dining, and with easy parking. The inn was historic, charming, and had lots of character. It was exactly what I was looking for. There is now staff available on premises from 7 am to 10 pm. I was able to check in on site. The outer doors were locked at night. I would definitely come back."

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"Loved the property, room was clean and had everything you needed!! We had an upgrade that was wonderful!! Only downfall was the outside little deck! No privacy all out In the open, side by side and facing the other units with a walkway in front of it!! Was looking forward to sitting out side but ended up not using it at all. "

Find out more about Sheffield

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Frequently asked questions

Can I find a vacation rental in Sheffield?

Yes, you can find vacation rentals near popular attractions in Sheffield, or you can select a more secluded option if you'd like a relaxing place to stay. Sheffield is known for its casinos and local tours.

What are some of the best vacation rentals that Sheffield has to offer?

Antique Farmhouse Totally Restored : This highly rated vacation home rental in Sheffield is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Sheffield?

With 26 Expedia vacation rentals, you're sure to find just the right place for your Sheffield stay.

What’s there to see and do in Sheffield?

Housatonic River and Mount Everett State Reservation are a couple of scenic spots to enjoy the outdoors, whereas Ashley House is one of the cultural attractions. While here, Magnolia Bluffs Casino and Thom Reed UFO Monument Park are other places worth a visit.

What are vacation rentals like in Sheffield?

Vacation rentals are private accommodations you can stay in for a couple days or more in Sheffield. Vacation rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip.

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Sheffield Vacation Rentals

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Check prices for these dates

Vacation Rentals in Sheffield

The Race Mountain House

Antique Farmhouse Totally Restored

Guesthouse Cabin vacation rentals in Berkshire County

The Ponds at Foxhollow

Spacious 5-bedroom house in charming Lee with WiFi

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

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Deluxe Queen Room with 2 Queen Beds

The Kemble- Built by a US Secretary of State in Lenox

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Hudson NY’S Country Serenity Guest Suite.

Lakefront Bungalow

Peace and quiet on the lake

Amore Estate - beautiful room with many places to explore and relax in.

Exclusive Estate, Heated Yearround Outdoor Pool

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Peaceful Retreat Compound 10 Minutes to Great Barrington!

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Top Sheffield Hotel Reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

The Whitlock

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Constance by the Lenox Collection

Quality Inn

The Red Lion Inn

Quality Inn

Howard Johnson by Wyndham Lenox

Find out more about Sheffield

Explore a world of travel with Expedia

Frequently asked questions