Sheffield Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 8 - Nov 9
Tomorrow
Nov 9 - Nov 10
Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23

Vacation Rentals in Sheffield

Dining
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield
10.0 out of 10, Exceptional, (9)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
United States
Robert B.
The price is ￥59,834
￥105,736 total
includes taxes & fees
Nov 10 - Nov 11
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
10.0 out of 10, Exceptional, (40)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥30,224
￥69,234 total
includes taxes & fees
Nov 10 - Nov 11
Cheerful 3-bedroom cottage with woodstove
Terrace/patio
Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.

2.0 star property
Chatham
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is ￥32,985
￥55,189 total
includes taxes & fees
Nov 11 - Nov 12
Sugar Shack - 300 square feet of pure sweetness.
Smart TV, fireplace
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

Chatham
10.0 out of 10, Exceptional, (9)
"We had the best time here. The house is even cuter and cozier in person (which says a lot because the pictures are great!). The hot tub was a great luxury and the house is literally a 3 minute walk to town. So convenient! We also had a fire in the Viking tent one night which was fun. Heidi was super helpful and quick to respond to any queries during our stay. She even left rose petals on the bed and a bottle of Prosecco chilling in the fridge for us upon our arrival. I would stay here again in a...
United States
Megan H.
The price is ￥34,520
￥63,320 total
includes taxes & fees
Nov 16 - Nov 17
HunnyHAUS: Deluxe TINY*private spa*walk to town
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town

Chatham
10.0 out of 10, Exceptional, (6)
"Perfect blend of decore, comfort, and function. We went to Tanglewood which was only a half hour away. Came back to hot tub and fire pit. Beds here are soooo comfy! This is our 2nd time here and won’t be our last."
United States
Melissa D.
The price is ￥32,985
￥55,361 total
includes taxes & fees
Nov 17 - Nov 18
BLUSH: Boutique TINY home*private spa*walk to town
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
The Ponds at Foxhollow
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
Goshen
9.8 out of 10, Exceptional, (7)
"Wonderful stay. It really is a gate house. The property is beautiful and the house is spacious. If I was eloquent,I could go on and on... "
United States
Wilford
The price is ￥18,104
￥99,984 total
includes taxes & fees
Nov 10 - Nov 11
CT Gate House Goshen CT, Gate House Goshen CT
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"We had a lovely one week stay at this property. The location was very convenient to all the restaurants and shops. The fall foliage was spectacular and truly enjoyed biking and hiking in the Berkshires."
United States
Farida K.
The price is ￥27,616
￥45,071 total
includes taxes & fees
Nov 17 - Nov 18
Home in Great Barrington
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (9)
"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 ￥24,578
￥60,185 total
includes taxes & fees
Nov 11 - Nov 12
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,369
￥57,889 total
includes taxes & fees
Nov 12 - Nov 13
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
8.8 out of 10, Excellent, (3)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ￥31,068
￥45,671 total
includes taxes & fees
Nov 10 - Nov 11
Pet Friendly Riverfront Home in Great Barrington
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Great Barrington Get Away

Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is ￥43,725
￥80,202 total
includes taxes & fees
Nov 10 - Nov 11
Great Barrington Get Away
TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

Hillsdale
9.2 out of 10, Wonderful, (5)
"The motel was well equipped, clean, and comfortable. It was especially suited for my travel with my dog."
United States
Susan S.
The price is ￥24,394
￥31,102 total
includes taxes & fees
Nov 10 - Nov 11
The Brooks Motel: Exceptional Suite
Exterior
Bungalow in the Berkshires

Bungalow in the Berkshires

Lee
10.0 out of 10, Exceptional, (4)
"Great location, very clean and well appointed with everyth"
United States
Nick R.
The price is ￥42,191
￥59,124 total
includes taxes & fees
Nov 30 - Dec 1
Bungalow in the Berkshires
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is ￥58,683
￥113,190 total
includes taxes & fees
Nov 15 - Nov 16
Spacious 5-bedroom house in charming Lee with WiFi
Interior
rural, serene + sophisticated space

rural, serene + sophisticated space

Red Hook
10.0 out of 10, Exceptional, (7)
"A beautifully curated barn overlooking a picturesque landscape. Gregg, the owner, really cares and wants to make sure you have everything you need. We stayed over a weekend when we were attending a wedding in the area. It was so nice to have a place to relax amidst all the festivities. The birdsong and bullfrog chorus led us to some of the soundest sleep we’ve enjoyed in a long time. "
United States
Kathryn
The price is ￥33,599
￥52,924 total
includes taxes & fees
Nov 11 - Nov 12
rural, serene + sophisticated space
Interior
The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley

Stanfordville
9.2 out of 10, Wonderful, (5)
"Our group had a lovely experience at this idyllic horse farm in the Hudson Valley. The rental was very well appointed and spacious on beautiful grounds. Communication with the property owner was friendly, welcoming and prompt which is always appreciated when arranging a joint family vacation! Would highly recommend as a picturesque escape from the City to any country loving folks!"
United States
Christina S.
The price is ￥88,370
￥142,317 total
includes taxes & fees
Nov 10 - Nov 11
The George is an elegant restored home in the Hudson Valley
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington
10.0 out of 10, Exceptional, (1)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥86,851
￥203,777 total
includes taxes & fees
Nov 10 - Nov 11
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington
The price is ￥52,163
￥88,427 total
includes taxes & fees
Nov 10 - Nov 11
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale
8.4 out of 10, Very Good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
The price is ￥42,651
￥96,549 total
includes taxes & fees
Dec 6 - Dec 7
Perfect House In Hillsdale, Brings Friends & Fam
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sheffield Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
Jamie 2-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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 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 25 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 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 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.