A covered wooden structure with a sloped roof, surrounded by greenery and trees.

Sheffield Vacation Rentals

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Sheffield vacation rentals

Property grounds

1. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 907
AED 1,908 total
includes taxes & fees
22 Sep - 23 Sep
Cheerful 3-bedroom cottage with woodstove
Coffee/tea maker, fridge, microwave, oven

2. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
The price is AED 413
AED 605 total
includes taxes & fees
8 Sep - 9 Sep
Cozy 1-bedroom studio in serene Great Barrington with AC
Coffee/tea maker, fridge, microwave, oven

3. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AED 992
AED 1,493 total
includes taxes & fees
3 Sep - 4 Sep
Home in Great Barrington
Desk, iron/ironing board, WiFi, bed sheets

4. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is AED 551
AED 708 total
includes taxes & fees
1 Sep - 2 Sep
The Brooks Motel: Exceptional Suite
Beach nearby, sun loungers, beach towels

5. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is AED 863
AED 1,333 total
includes taxes & fees
14 Sep - 15 Sep
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Lobby

6. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,105 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is AED 295
AED 412 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Interior

7. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AED 744
AED 1,155 total
includes taxes & fees
8 Sep - 9 Sep
Cozy Riverside Berkshires Retreat
Interior

8. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AED 643
AED 1,173 total
includes taxes & fees
1 Sep - 2 Sep
Sweet Cozy Victorian in Housatonic. Close to everything.
3 bedrooms, iron/ironing board, WiFi, bed sheets

9. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is AED 1,174
AED 2,049 total
includes taxes & fees
8 Sep - 9 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Interior

10. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very Good, (1 review)
The price is AED 176
AED 1,042 total
includes taxes & fees
13 Sep - 14 Sep
Real Estate: Therapy - Lake, Laundry, Love it
Desk, iron/ironing board, WiFi, bed sheets

11. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very Good, (8 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is AED 580
AED 745 total
includes taxes & fees
1 Sep - 2 Sep
The Brooks Motel: Exceptional Suite
Smart TV, books

12. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is AED 1,483
AED 2,484 total
includes taxes & fees
1 Sep - 2 Sep
Fantastic 2-bedroom house with AC in quaint Hillsdale.
TV

13. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AED 1,036
AED 2,139 total
includes taxes & fees
21 Sep - 22 Sep
Treetop Hideaway in Tyringham
Terrace/patio

14. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is AED 463
AED 881 total
includes taxes & fees
1 Sep - 2 Sep
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Terrace/patio

15. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
The price is AED 625
AED 801 total
includes taxes & fees
14 Sep - 15 Sep
Cozy Camper tucked into the woods
Interior

16. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 536
AED 1,386 total
includes taxes & fees
9 Sep - 10 Sep
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
TV, fireplace, printers

17. 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, (7 reviews)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
The price is AED 2,089
AED 4,869 total
includes taxes & fees
1 Sep - 2 Sep
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Smart TV

18. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.4 out of 10, Exceptional, (6 reviews)
The price is AED 655
AED 1,494 total
includes taxes & fees
8 Sep - 9 Sep
stylish Berkshires Retreat
Outdoor spa tub

19. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 588
AED 1,457 total
includes taxes & fees
7 Sep - 8 Sep
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
2 bedrooms, WiFi (free), bed sheets

20. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is AED 456
AED 824 total
includes taxes & fees
1 Sep - 2 Sep
Peaceful and cozy 1 bed 1 bath in quaint Winchester
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"
William 2-night trip
Posted 1 hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home near Sheffield is located near skiing 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. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Sheffield?

With 23 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, Three Mile Pond Wildlife Management Area 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.