Holiday Rentals in Sheffield

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Holiday Rentals in Sheffield

Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is €468
includes taxes & fees
8 Oct - 9 Oct
Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (82)
"We had 15 people stay for three nights for a family reunion - 9 adults and 6 kids. The house worked well, as all had reasonably private spaces. The countryside is beautiful. Visits to a lake for swimming and several local waterfalls worked well for all."
Antique Farmhouse Totally Restored
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (206)
"My best friend and I had a much needed break. It was a great stay! Thank you!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
"Our mix of family and friends had a wonderful time at your home over the Labor Day weekend. The space was clean, spacious and beautiful. The property had plenty for everyone to do. We will definitely be booking again. "
Amore Estate - beautiful room with many places to explore and relax in.
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (10)
"This was the perfect place for enjoying our visit with our adult children! Very well appointed home and we had a very lovely visit! Peaceful and lovely location!"
Pristine Home In Becket Woods
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (30)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
9.8 out of 10, Exceptional, (37)
"Communication with property manager was seamless, and above any previous interactions I have ever had. Great place. Well maintained. Clean. Stocked with basic kitchenware and cleaning material. Great Wifi. Tennis Court was such a nice bonus. Would 100% (and will likely) stay here again!"
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (13)
"The country setting provided a quiet retreat. The home is well equipped: plenty of beds, multiple gathering places, pool with towels (although it was pretty cold until the pool guy came and provided help). The outdoor grill provides additional cooking space. The home is within easy driving to many places of interest. We had a nice week at this home."
Private Estate, Heated YEARROUND Outdoor Pool
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.6 out of 10, Exceptional, (13)
"Me and my husband and my sister and her husband came to the Hudson Valley to place a bench in his hometown in his memory. We thoroughly enjoyed our time at this property. It was just exactly what we needed-quiet and relaxing!"
The price is €310
includes taxes & fees
6 Oct - 7 Oct
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Peace and quiet on the lake
9.6 out of 10, Exceptional, (192)
"Nice quiet house and neighborhood. "
Peace and quiet on the lake
Private Island - Largest Fresh Water Reservoir in Mass....
9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, (78)
"My fiancé and I had an amazing stay at this cabin. Very quiet and peaceful and lots to do just on the property alone. The host Karen was very nice and welcoming, left us ice cream sundaes and set up a birthday sign for my fiancé on our arrival! Beautiful cabin and very private, we will definitely be back! "
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, (132)
"Quiet and secluded, but close to everything you may need and plenty of wildlife to observe."
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Fox Hollow Luxury Ranch Laurel Lake
8.8 out of 10, Excellent, (16)
"Very quiet central location in the Berkshires. Close to all amenities. Enjoyed the lake canoeing and site seeing. Great house with everything needed. "
Fox Hollow Luxury Ranch Laurel Lake
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
9.4 out of 10, Exceptional, (34)
"My grown daughter and I stayed here for a two night visit to the Berkshires. It was so nice to have an entire house rather than a hotel room! We received our check in email in plenty of time, the house was clean and furnished with generous amenities such as soaps, shampoos, coffee, etc., the owner was readily available. The house is close to the road, but it really wasn’t a problem…white noise machines and air purifiers made sleeping very comfortable, and there was very little traffic noise....
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (40)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (8)
"This is my second summer renting this house. It's great. Beautiful home, lots of light, in the woods, very comfortable. Our first year we had a rainy Sunday and it was fun to just hang out in. Very clean. The rental contact person was very responsive to a question we had. Five minutes from Jacob's Pillow. Lenox/Lee/Stockbridge are all just a quick drive away. Very quiet rural setting. A deer visited us this year, early on Sunday morning. Love this place."
Berkshires Cabin 2 Mi to Appalachian Trail!
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (141)
"Great place and views. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
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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.
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Other types of properties in Sheffield you may be interested in

Race Brook Lodge
2.0 star property
8.8 out of 10, Excellent, (26)
"Cozy and rustic, the room had a lot of character, antique rugs/furnishings, old pine floors, and exposed wooden beams on the ceiling- cute cabin/cottagecore vibes! beautiful property with lots of trees, close to hiking trails, short drive to other attractions. Breakfast buffet was great too! "
The price is €202
includes taxes & fees
15 Oct - 16 Oct
Race Brook Lodge
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (404)
"Third stay at property, so we know what to expect. It's a nicely reimagined/updated 2-story motel on the outskirts of Lenox. When present, staff is nice and efficient, but be prepared to deal with texts, QR codes and receiving auto replies when any issues arise. We had a pleasant overnight and enjoyed breakfast from the limited menu. (Usually we go to one of several excellent local cafés.) Our only problem was the inability of onsite staff or offsite administration to refund our original...
The price is €163
includes taxes & fees
16 Oct - 17 Oct
Life House Berkshires
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (994)
"The Red Lion Inn is a gem of the Berkshires. It is a warm, welcoming place."
The price is €315
includes taxes & fees
9 Oct - 10 Oct
The Red Lion Inn
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.

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?

Pristine Home In Becket Woods: This holiday home rental outside Sheffield is located near skiing, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a private garden and a selection of books.

How many holiday rentals are there in Sheffield?

With 18 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 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 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.