Search Holiday Rentals in Sheffield

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Top Holiday Rentals in Sheffield

Cheerful 3-bedroom cottage with woodstove
Property grounds
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (21)
"We rented for the winter to use on the weekends. Sabrina was very responsive and thoughtful throughout. The house is incredibly well stocked and thoughtfully organized. Two seating areas downstairs made it easy for our family of four to spread out, even when we had guests. Kitchen is well laid out, mattresses are very comfortable, and the surrounding area is quiet. We would definitely go back."
The price is £368
includes taxes & fees
2 May - 3 May
Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
Exterior
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (78)
"Really nice farmhouse with plenty of room and eclectic decor. Robin was a responsive host. Would strongly recommend."
Antique Farmhouse Totally Restored
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
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The Freeman - Newly Renovated 14K SF Estate on 40 Acres
7 bedrooms, iron/ironing board, cots/infant beds, travel cot
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (28)
"We've stayed in a lot of home rentals - and across the board - this was the best place ever. The home was clean, nicely decorated and super comfortable. The hosts were easy to get a hold of and incredibly welcoming, leaving us with a generous basket of local treats. We loved the peaceful outdoor space and roamed all 40 acres. The pond was beautiful and if it had only been warmer we'd have jumped in the rowboat. We will be back for sure. A++ Thank you, Anna!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (10)
"The hosts have made this ranch house into an artsy, cozy place for families to rest and relax! Plenty of space for family hang outs and game playing, but also enough rooms for tweens or teens to get away and have alone time. Beautiful spaces throughout. We would have loved to enjoy the backyard space and screened-in porch if it hadn't been winter, but appreciated watching the snow falling while sipping coffee by the kitchen window! Close to Catamount ski area and minutes from Stockbridge shops...
Stockbridge Home, Come Experience The Berkshires!
Serene Acreage - Pond - Hiking Trails Nearby
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
Property grounds
Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
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 - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
Romantic and Secluded Berkshire's Gem
Fridge, microwave, oven, stovetop
Romantic and Secluded Berkshire's Gem
10.0 out of 10, Exceptional, (9)
"My friends and I had an amazing time staying in the cozy cabin. 9 of us slept comfortably, the place was spotless, and so cute. We hope to visit again."
Romantic and Secluded Berkshire's Gem
Cozy Cabin in the Berkshires
Property grounds
Cozy Cabin in the Berkshires
10.0 out of 10, Exceptional, (3)
"Cant wait to book again. Great place for familys. Owner thinks of everything that you would need during your stay."
Cozy Cabin in the Berkshires
Quintessential 6-BR Berkshires Lodge
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"The house was perfect and Sydney was a great host. "
Quintessential 6-BR Berkshires Lodge
The Winthrop Estate - 12K SF 32 Acres
Exterior
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, (2)
"Absolutely stunning property - truly incredible stay. Recommend to anyone looking for a large group getaway. Fast WiFi, commercial grade kitchen and plentiful supplies make it easy for large groups. beautiful property and room for activities on a huge lawn. Highly recommend."
The Winthrop Estate - 12K SF 32 Acres
Beautiful retreat to the woods to enjoy the winter season.
Aerial view
Beautiful retreat to the woods to enjoy the winter season.
10.0 out of 10, Exceptional, (31)
"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."
Beautiful retreat to the woods to enjoy the winter season.
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
Moose Lodge by AvantStay | Luxe Berkshires Escape
Outdoor dining
Moose Lodge by AvantStay | Luxe Berkshires Escape
9.8 out of 10, Exceptional, (10)
"It was unique, with unusual amenities, like the home theater and fabulous game room. Our weather was wintery, so this was such a comfortable and fun way for the family to spend time together!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
Berkshires Cabin 2 Mi to Appalachian Trail!
Interior
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Bar (on property)
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, (68)
"The cabin was wonderful and was stocked will everything we needed and more. The lake was both beautiful and private to just this cabin. The grounds had several trails that we enjoyed."
Romantic Log Cabin on Privately-Owned Lake with Fireplace
The Meadows House @ Otis Ridge w/ 7-person hot tub
Property grounds
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (20)
"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (181)
"Thank you, Justin, for sharing your beautiful home with my family. We had a very nice time and relaxed in the beautiful quiet surroundings. I was so excited when I saw some Norwex items as I am a consultant and also use Norwex in my home. We hope to visit again in the warmer months as it was a perfect memory for our family. Thanks again, The Short family"
Peace and quiet on the lake
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (194)
"The house is beautifully remodeled and clean. Nice open area with all like new kitchen appliances. My friend and I are thinking of going back in the summer to enjoy the lake"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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 £220
includes taxes & fees
14 May - 15 May
Perfect Vacation Get Away - Historical New Marlborough
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See all available properties in Sheffield
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 Holiday Rental Travel Info

Number of holiday rentals
5
Popular accommodation
Sheffield private holiday homes
Known landmarks
Bash Bish Falls State Park, Les Trois Emme Winery and Umpachene Falls Park
International airports
Hartford, CT (BDL-Bradley Intl.), Albany, NY (ALB-Albany Intl.) and Hartford, CT (HFD-Hartford - Brainard)

Other types of properties in Sheffield you may be interested in

Race Brook Lodge
Exterior
Race Brook Lodge
2.0 star property
9.4 out of 10, Exceptional, (8)
"It was quiet setting by the rooms are run down "
The price is £147
includes taxes & fees
12 May - 13 May
Race Brook Lodge
Life House Berkshires
Lobby
Life House Berkshires
3.5 star property
9.2 out of 10, Wonderful, (231)
"Very accommodating and friendly staff. Coffee in the morning was excellent. "
The price is £89
includes taxes & fees
5 May - 6 May
Life House Berkshires
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Just a nice, cozy and very clean little hotel. We would stay there again if in the area."
The price is £90
includes taxes & fees
9 May - 10 May
The Black Swan Lee - Lenox, Ascend Hotel Collection
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.

Everything you need to know about Sheffield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sheffield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sheffield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sheffield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sheffield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sheffield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sheffield holiday rentals we have selected for you start as low as £368 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sheffield rentals

At Expedia, we put the best Sheffield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sheffield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sheffield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sheffield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Sheffield?

Yes, there are holiday rentals close to the most popular sights in Sheffield, or you can select a more secluded option if you're looking for a relaxing stay. Sheffield is known for its casinos and local tours.

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

Fox Hollow Luxury Ranch Laurel Lake: This holiday home rental outside Sheffield is located on a lake, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Sheffield?

With 25 Expedia holiday rentals, you're guaranteed to find just the right place for your Sheffield stay.

What’s there to see and do in Sheffield?

Housatonic River and Thom Reed UFO Monument Park 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 Mount Everett State Reservation are other places worth a visit.

What are holiday rentals like in Sheffield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sheffield. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family getaway.

Recent reviews of Sheffield properties
Expedia verified reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"Just a nice, cozy and very clean little hotel. We would stay there again if in the area."
A verified traveller from Marion stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 11 hours ago
The Black Swan Lee - Lenox, Ascend Hotel Collection