Search Apartments in Sheffield

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

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

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Living area

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.2 out of 10, Wonderful, (12)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
Living area

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect location. Walking distance. Brand new apartment. "
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
The Penthouse, Downtown Lenox by Evergreen Home
Gorgeous open concept living room

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (7)
"This is the second year we had our girls weekend at the Penthouse and it did not disappoint. The place is updated, very clean, and in a great location! Only suggestion would to get a nice big sectional couch! We had 8 people and not enough comfy seating. But beautiful apartment!! "
The Penthouse, Downtown Lenox by Evergreen Home
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts
living area open to kitchen

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

10.0 out of 10, Exceptional, (1)
"Lovely quiet spot with plenty of eating options around the area. Well maintained."
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
Exterior

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

9.4 out of 10, Exceptional, (12)
"We had a great trip to this lovely home! Clean and cute, near beautiful nature and easy access to grocery stores."
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
Modern Copake Falls Getaway
Interior

Modern Copake Falls Getaway

9.6 out of 10, Exceptional, (29)
"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
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Room

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

9.2 out of 10, Wonderful, (38)
"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.
Baldwin Hill Retreat Guest House
Living area

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
Renovated Downtown 1bedroom
Living area

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (22)
"We’ve always had a great experience with Downtown Upstairs in Lenox and this was no exception. Easy access to the downtown stores and restaurants with the comfort of a nice, clean, well furnished apartment. "
Renovated Downtown 1bedroom
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Exterior

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

9.4 out of 10, Exceptional, (60)
"The property was fine for our purposes of visiting family. If we needed to cook, it would have been quite difficult, though not totally impossible. The furniture was comfortable and the rooms, except the kitchen, had plenty of space. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Lovely bright apartment in pastoral shaker barn
Welcome to Dublinshire Farm, apartment one!

Lovely bright apartment in pastoral shaker barn

10.0 out of 10, Exceptional, (2)
"We traveled from Arizona for a class reunion and stayed in apartment. The property was clean and well appointed. We were able to host a dinner with four family members we had not seen in years! Another highlight was sitting outside by the fire pit in the evening. The property host, Michelle, provided excellent check in instructions and answered any questions very promptly. This property worked out very well for us, but if you have an issue with stairs you might want to check out the other...
Lovely bright apartment in pastoral shaker barn
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock
House and waterfront yard with dock

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
51 Church Street, Lenox MA - One Bedroom Unit
Living area

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (24)
"Lovely apartment in a great location "
51 Church Street, Lenox MA - One Bedroom Unit
Gateway to the Berkshires - Renovated downtown apartment
Room

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (7)
"Thanks, Emmy, for a great visit. The apartment was exactly what we hoped for, clean and convenient to downtown and to all things in the Berkshires. We explored and relaxed and thoroughly enjoyed our getaway over a beautiful October weekend. I'd recommend the apartment to anyone who wants that in-town setting and wishes to explore all that the area has to offer. Great host, thank you!"
Gateway to the Berkshires - Renovated downtown apartment
Garfield House Studio at 208
Exterior

Garfield House Studio at 208

9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
Garfield House Studio at 208
Dugway Hideaway Walking Distance to Lime Rock Park

Dugway Hideaway Walking Distance to Lime Rock Park

9.0 out of 10, Wonderful, (10)
"Enjoyed another cozy stay at this property!"
The price is SAR 750
SAR 1,198 total
includes taxes & fees
4 Feb - 5 Feb
Dugway Hideaway Walking Distance to Lime Rock Park
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Interior

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

9.8 out of 10, Exceptional, (7)
"Comfortable and spacious, in a lovely setting. "
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Apartment in Gorgeous Stonybrook Farm

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
Upstairs on Main
Exterior

Upstairs on Main

9.2 out of 10, Wonderful, (31)
"Check in was easy, beds are comfortable. I’m a big and tall guy, so only qualm I had was the small toilet, and low shower head. Aside from those, great stay!"
Upstairs on Main
Private hot tub + Modern Cottage
Room

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.
Don't see what you're looking for?
See all available properties in Sheffield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
Property grounds

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
The price is SAR 1,969
SAR 3,352 total
includes taxes & fees
4 Feb - 5 Feb
Guesthouse Cabin vacation rentals in Berkshire County
The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is SAR 897
SAR 1,002 total
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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 29 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?
Below are some of the favorite apartments in the area to choose from: Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Situated in Great Barrington, 5.9 mi/9.6 km from the heart of Sheffield. Includes free WiFi, separate dining areas, and Smart TVs. 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. Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge: It’s located in Stockbridge, 12.1 mi/19.4 km away. The Penthouse, Downtown Lenox by Evergreen Home: 17.5 mi/28.2 km away in Lenox. Free WiFi and Smart TVs are included. Lovely bright apartment in pastoral shaker barn: It’s located in Richmond, 21.1 mi/33.9 km from Sheffield. Includes free WiFi and Smart TVs.
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 Bartholomews Cobble are a couple of scenic spots to enjoy the outdoors, whereas Ashley House is one of the cultural attractions. Magnolia Bluffs Casino 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.