Sheffield Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Sheffield holiday rentals

Exterior
Antique Farmhouse Totally Restored

Holiday Home in Sheffield

Antique Farmhouse Totally Restored
9.8 out of 10, Exceptional, (94)
"The property was beautiful. Very spacious, inside and out. "
United States
Michelle C.
Antique Farmhouse Totally Restored
Interior
Guesthouse Cabin vacation rentals in Berkshire County

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is HK$3,190
HK$5,518 total
includes taxes & fees
21 Dec - 22 Dec
Guesthouse Cabin vacation rentals in Berkshire County
Front of property – evening/night
The Ponds at Foxhollow

Condo resort in Lenox

The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (136)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow
Interior
Pet Friendly Riverfront Home in Great Barrington

Holiday Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington
9.4 out of 10, Exceptional, (6)
The price is HK$1,575
HK$2,316 total
includes taxes & fees
15 Dec - 16 Dec
Pet Friendly Riverfront Home in Great Barrington
TV, DVD player, books, video library
Peace and quiet on the lake

Holiday Home in Sherwood Forest

Peace and quiet on the lake
9.6 out of 10, Exceptional, (230)
"Great communication, comfortable home, love the location"
United States
Susan C.
Peace and quiet on the lake
Exterior
The Kemble- Built by a US Secretary of State in Lenox

Villa in Lenox

The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox
Interior
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Apartment in Great Barrington

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
9.6 out of 10, Exceptional, (38)
"The apartment has everything you might need for a comfortable stay. Perfect location. The host is very responsive and always ready to help. The place is very clean and beautiful. I highly recommend it and will be happy to come back next year. "
United States
Elena
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Fridge, microwave, oven, stovetop
Spacious 5-bedroom house in charming Lee with WiFi

Holiday Home in Lee

Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is HK$2,976
HK$5,783 total
includes taxes & fees
18 Dec - 19 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Terrace/patio
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Holiday Home in Cornwall

Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
9.6 out of 10, Exceptional, (53)
"Great house and great stay!"
United States
Timothy P.
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Holiday Home in Stockbridge

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (135)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Smart TV, fireplace, table football, books
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Holiday Home in Great Barrington

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
10.0 out of 10, Exceptional, (54)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Holiday Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,135
HK$2,910 total
includes taxes & fees
15 Dec - 16 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Holiday Home in Great Barrington

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Interior
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Holiday Home in Egremont

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
9.8 out of 10, Exceptional, (25)
"Farmhouse was as pictured and very clean. Grounds and location were gorgeous "
United States
kathy l.
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Interior
Amore Estate - beautiful room with many places to explore and relax in.

Holiday Home in Lenox

Amore Estate - beautiful room with many places to explore and relax in.
9.2 out of 10, Wonderful, (33)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.
Smart TV, books
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Holiday Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is HK$1,247
HK$3,036 total
includes taxes & fees
15 Dec - 16 Dec
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Outdoor dining
The Goshen Glass Chalet

Holiday Home in Goshen

The Goshen Glass Chalet
9.6 out of 10, Exceptional, (42)
"The place was very nice met all of our expectations. "
United States
Marie G.
The Goshen Glass Chalet
Exterior
The Blue Elm - A Historic Berkshire Cottage

Cottage in Sheffield

The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (15)
"It was wonderful!! The hosts were fantastic and the place was lovely. Highly recommend. "
United States
noel s.
The Blue Elm - A Historic Berkshire Cottage
Exterior
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Apartment in Lee

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
9.4 out of 10, Exceptional, (71)
"Wonderful time !! Location was perfect and we really enjoyed our time here "
United States
Sue P.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Property grounds
Remodeled Lakefront retreat!!! Don't forget to book for ski season!

Holiday Home in Copake

Remodeled Lakefront retreat!!! Don't forget to book for ski season!
9.8 out of 10, Exceptional, (14)
"We skied, we played in the snow and overall just relaxed at this perfect home!"
United States
Melissa D.
Remodeled Lakefront retreat!!! Don't forget to book for ski season!
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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Top Sheffield Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"The rooms were clean and comfortable and the staff mostly friendly (the bartender one night was less-than-welcoming and kept trying to rush us out.) Would stay again!"
Madeleine 1-night trip
Posted 3 days ago
Berkshires Untold

Find out more about Sheffield

Search for holiday rentals in Sheffield on Expedia! You can easily find your home rentals, villas, holiday apartments in Sheffield using one of the methods below:

  • View our selection of featured holiday rentals in Sheffield
  • Use the map to find apartments and other holiday homes in the Sheffield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sheffield while they last

Look no further and take a look at our great range of rental properties in Sheffield!

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?

Antique Farmhouse Totally Restored : This highly rated holiday home rental in Sheffield is located in a rural location, and has a fireplace, a patio 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 garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Sheffield?

With 26 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 Three Mile Pond Wildlife Management Area 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.