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

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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 apartments

Coffee/tea maker, fridge, microwave, oven

1. 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)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is AED 413
AED 605 total
includes taxes & fees
3 Sep - 4 Sep
Cozy 1-bedroom studio in serene Great Barrington with AC
Desk, iron/ironing board, WiFi, bed sheets

2. 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
30 Aug - 31 Aug
The Brooks Motel: Exceptional Suite
Beach nearby, sun loungers, beach towels

3. 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 867
AED 1,338 total
includes taxes & fees
13 Sep - 14 Sep
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
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
30 Aug - 31 Aug
The Brooks Motel: Exceptional Suite
Terrace/patio

5. 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.
Living area

6. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is AED 807
AED 1,266 total
includes taxes & fees
31 Aug - 1 Sep
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Pool

7. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.0 out of 10, Wonderful, (4 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is AED 731
AED 1,407 total
includes taxes & fees
1 Sep - 2 Sep
Hudson NY’S Country Serenity Guest Suite.
Interior

8. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
The price is AED 826
AED 1,173 total
includes taxes & fees
30 Aug - 31 Aug
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great visit to Stockbridge. Can't think of a better place to stay than the iconic Red Lion Inn."
Daniel 2-night trip
Posted 10 hours ago
The Red Lion Inn

Frequently asked questions

What's it like to stay at an apartment in Sheffield?
You'll find plenty of places to stay in Sheffield with 32 accommodations. Though there aren't many apartments, we can help you find similar accommodations. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can also filter by similar properties such as vacation homes, condos, or cabins.
Why should you consider an apartment versus a traditional hotel?
Often more spacious than a traditional hotel room, an apartment comes with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for couples who want to stay away from the tourist areas.
What's the best apartment for my stay in Sheffield?
Here are some of the more popular apartments in the area: Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts: Includes Smart TVs. Access to onsite laundry facilities is available on site. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake: Located 6.6 mi/10.6 km away in Great Barrington. Free WiFi, private balconies, and Smart TVs are included. Access to onsite laundry facilities is available on site. Cozy 1-bedroom studio in serene Great Barrington with AC: Located in Great Barrington, 5.6 mi/9.1 km away. Includes free WiFi, private balconies, and Smart TVs. Access to onsite laundry facilities is available on site. Cozy 1-bedroom apartment in old farm house in historic South Lee: Located 12 mi/19.4 km away in South Lee. Amenities include private patios. Access to onsite laundry facilities is available on site.
What will the weather be like in Sheffield?
Though weather is just one factor, it can really affect your travel plans, especially when you are planning a longer stay in Sheffield. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What are the must-see places to visit 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. Three Mile Pond Wildlife Management Area and Mount Everett State Reservation are other places to visit while you're in town.
What's the best way to get to and around Sheffield?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.