Search Apartments in Sheffield

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Compare 55 Apartments in Sheffield with updated reviews, rates, and availability.

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (59)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.6 out of 10, Exceptional, (8)
"Super cute, cozy and excellent location. Loved our stay. Will be back!"
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Modern Copake Falls Getaway

9.8 out of 10, Exceptional, (27)
"Unbeatable accommodations, especially for the price. Would stay again, gorgeous sunrise and sunset, very peaceful. Wish I could live there part time!"
Modern Copake Falls Getaway

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (6)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home

Charming 2-bedroom apartment in downtown Stockbridge with AC, WiFi

Charming 2-bedroom apartment in downtown Stockbridge with AC, WiFi

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

10.0 out of 10, Exceptional, (6)
"Comfortable and spacious, in a lovely setting. "
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Restored 19th century farmhouse apartment 2 -charming farmland and town culture!

9.4 out of 10, Exceptional, (11)
"Cute, quite apartment on the second floor. Enjoyed coffee on the small deck looking out at the farm animals on a cool, crisp and sunny fall morning. Perfect place as base camp for our weekend adventures in the area!"
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!

Main Street Delight 1bedroom

10.0 out of 10, Exceptional, (18)
"The location was fantastic for our stay in the Berkshires. Walkable to many restaurants & shops. It was very well decorated & cozy. Very convenient being above a coffee shop, however not ideal if you enjoy sleeping in. We could hear the consistent squeaking of the coffee shop door as soon as it opened in the morning (~7:00 am) from the bedroom. However, good motivation to get up and enjoy the beautiful Berkshires!"
Main Street Delight 1bedroom

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (21)
"Location, location, location. Great use of space in this nicely decorated, conveniently located apt. Steps away from restaurants and shopping. 7 minutes from Kripalu. Great communication from owner. Looking forward to next stay."
Renovated Downtown 1bedroom

Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

2.0 star property
10.0 out of 10, Exceptional, (2)
"Very clean and nicely decorated apartment in center of town. Great location. Really enjoyed our vacation."
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

Baldwin Hill Retreat Guest House

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property and neighborhood were gorgeous! Walkable roads with low speed limits and a nearby park were major bonuses. Plenty of food options nearby, and downtown Great Barrington is only a short drive away. The house was super clean, gorgeously furnished, and very cozy. The beds and linens were very good quality and I had an incredibly restful stay. I will certainly be renting this spot for my next trip to the area! "
Baldwin Hill Retreat Guest House

The Brooks Motel: Exceptional Suite

10.0 out of 10, Exceptional, (2)
"The motel was well equipped, clean, and comfortable. It was especially suited for my travel with my dog."
The price is AED 584
AED 704 total
includes taxes & fees
30 Nov - 1 Dec
The Brooks Motel: Exceptional Suite

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

9.2 out of 10, Wonderful, (37)
"We loved the brilliant use of space and all the amenities in this cozy hideaway. My husband, who owns a Professional Organization business, was very pleased and impressed by the clever use of various storage options. The walkways were attractively and effectively lit up for evening strolls and dog walking. All instructions were clearly communicated and our stay was lovely"
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Garfield House Studio at 208

9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
Garfield House Studio at 208

Apartment in Gorgeous Stonybrook Farm

9.4 out of 10, Exceptional, (44)
"This was a beautifully appointed property on an estate overlooking a pond. The apartment was spotless and the caretaker was most helpful when we needed anything. The rooms were well supplied and perfect for us. Thank you for letting us experience the quintessence of the Berkshires."
Apartment in Gorgeous Stonybrook Farm

Private apartment in beautiful country barn

10.0 out of 10, Exceptional, (18)
"Great farmhouse in the Berkshires. Location is out of the way without being out of the way. Communications with the host is great. Very accommodating."
Private apartment in beautiful country barn

The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock

9.6 out of 10, Exceptional, (8)
"We had a great time at Highland Lake. The apartment was so comfortable, and larger than I would have thought from the description. It was convenient to town - the teens loved access to DQ, pizza shops, etc just a few minutes away. There were kayaks and a paddleboat we could borrow, which I somehow missed in the description - nice pluses! The lake access from the dock was perfect. We brought stand-up paddleboards, and had an easy time launching them and exploring the lake. In the apartment,...
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock

The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock

9.8 out of 10, Exceptional, (9)
"Perfect for our visit to our children and grand children. The lake is across the street with the marina next door. Rented a pontoon boat, at a discounted rate for beautiful day with the kids. Minor problem getting in initially, but resolved by Jeanne quickly. Note that this is a renovated lake residence which has a second story rental which can get a bit noisy and the bathroom is in the rear of the house with the bedroom in the front. Overall will be returning in the future."
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock

Dugway Hideaway Walking Distance to Lime Rock Park

9.0 out of 10, Wonderful, (9)
"Great location and super easy to navigate!"
The price is AED 735
AED 1,185 total
includes taxes & fees
27 Nov - 28 Nov
Dugway Hideaway Walking Distance to Lime Rock Park

Private hot tub + Modern Cottage

10.0 out of 10, Exceptional, (5)
"The accommodation is exactly as it appears in the photos, although with no house number it took us a while to locate the specific property on the road. It’s great that we could take our dog and he loved it too. Claverack is an ideal location for Hudson. "
Private hot tub + Modern Cottage
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 property types in Sheffield

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (30)
"Delightful home in very quiet neighborhood near hiking trails. House had every amenity you might need (except tissues). Less than 20 minutes drive from Sheffield. Great restaurants in town. We very much enjoyed our stay in this house in the country and would highly recommend it to anyone wanting to stay in the area."
The price is AED 871
AED 1,863 total
includes taxes & fees
4 Dec - 5 Dec
Cheerful 3-bedroom cottage with woodstove

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake
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

What's it like to stay at an apartment in Sheffield?
You’ll find plenty of places to stay in Sheffield with 26 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: Remodeled Unit #2, 7 min to Great Barrington, 12 min to Ski Resorts & Trails: Includes free WiFi and private patios. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 14.7 mi/23.6 km away in Lee. Private patios and fireplaces are included. Enjoy a restful stay with fast internet, smart TV and the company of your pet.: It’s situated in Winsted, 19.5 mi/31.3 km away. Includes free WiFi, fireplaces, and Smart TVs. Garfield House Studio at 208: 14.7 mi/23.7 km away in Lee. Amenities include private patios. Modern Copake Falls Getaway: It’s located in Copake Falls, 8.4 mi/13.5 km from Sheffield. Includes private patios and fireplaces.
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 Mount Everett State Reservation are a couple of scenic spots to enjoy the outdoors, whereas Ashley House is one of the cultural attractions. Magnolia Bluffs Casino and Drury Preserve 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.