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Check prices for these dates

Next weekend
21 Rab. I - 23 Rab. I
In two weeks
28 Rab. I - 30 Rab. I
In one month
11 Rab. II - 13 Rab. II
In two months
9 Jum. I - 11 Jum. I

Compare 57 Apartments in Sheffield with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Food and drink

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (14)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock
Property grounds

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

9.6 out of 10, Exceptional, (9)
"The house was very friendly. We had a beautiful view with the lake and a snowstorm that we were able to watch. It was great seeing the fisherman and the snowmobiles on the lake. Our group made some nice meals together and we really were relaxed. The home was very comfortable."
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Golf

1500 sqft private entrance with beautiful views of the Berkshire Mountains

10.0 out of 10, Exceptional, (41)
"My husband and I stayed at this clean, spacious, and well-equipped apartment adjacent to the hosts' home for three nights to visit nearby attractions in Lenox, Pittsfield, Great Barrington, and Stockbridge. It was a wonderful property and the hosts couldn't have been nicer. We especially loved the gift basket prepared with some of their favorite area treats. Communication about the check-in/check-out process was simple. FYI for future travelers: there are no bathroom toiletries provided so...
1500 sqft private entrance with beautiful views of the Berkshire Mountains
The Studio mini home away from home in the Berkshires
Outdoor dining

The Studio mini home away from home in the Berkshires

9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
The Studio mini home away from home in the Berkshires
51 Church Street, Lenox MA - One Bedroom Unit
Fridge, microwave, oven, stovetop

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (26)
"Great location. Well appointed. Pictures don’t really do this place justice. "
51 Church Street, Lenox MA - One Bedroom Unit
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
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, (61)
"3 day holiday getaway, my husband and our 2 pups. A hike in nearby trails in the woods, enjoyed Lee downtown eateries and shops. Beautiful winter wonderland in the Berkshires. The guest rental was perfect!!! Warm, spacious, comfortable, perfect location. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Gateway to the Berkshires - Renovated downtown apartment
1 bedroom, free WiFi, bed sheets

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
Upstairs on Main with private bathroom
Property grounds

Upstairs on Main with private bathroom

9.2 out of 10, Wonderful, (32)
"We enjoyed our stay in this great place! cute little upstairs apartment with a great use of space and perfect for getting around the area. We got the benefit of a beautiful snow storm too (and the walk and parking area were shoveled when we woke up which was nice!) thanks again."
Upstairs on Main with private bathroom
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
Property grounds

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

9.4 out of 10, Exceptional, (13)
"Cute little apartment in a cute and quiet street. Loved our stay!"
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
Hudson NY’S Country Serenity
Property grounds

Hudson NY’S Country Serenity

10.0 out of 10, Exceptional, (1)
"Quiet, private , comfortable and clean sanctuary! Highly recommend…!! "
Hudson NY’S Country Serenity
Heart of Lenox!! - renovated downtown apartment
Flat-screen TV

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (68)
"The place was beautiful and comfortable. Everything was new and clean. Loved the location. Thanks again."
Heart of Lenox!! - renovated downtown apartment
Renovated Downtown 1bedroom
Stovetop, dishwasher

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
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts
Fridge, microwave, oven, stovetop

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
Apartment in Gorgeous Stonybrook Farm
1 bedroom, in-room safe, iron/ironing board, free WiFi

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
The Brooks Motel: Exceptional Suite
TV, offices

The Brooks Motel: Exceptional Suite

9.4 out of 10, Exceptional, (3)
"The motel was well equipped, clean, and comfortable. It was especially suited for my travel with my dog."
The price is SAR 525
SAR 642 total
includes taxes & fees
11 Mar - 12 Mar
The Brooks Motel: Exceptional Suite
Brooks Motel: Perfect Suite, Seasonal Waterviews
Property grounds

Brooks Motel: Perfect Suite, Seasonal Waterviews

The price is SAR 476
SAR 609 total
includes taxes & fees
11 Mar - 12 Mar
Brooks Motel: Perfect Suite, Seasonal Waterviews
Dugway Hideaway Walking Distance to Lime Rock Park
Golf

Dugway Hideaway Walking Distance to Lime Rock Park

9.2 out of 10, Wonderful, (11)
"My partner and I stayed here overnight for a nearby wedding in Salisbury. The property was easy to find and conveniently located near main roads for the area. The hosts are very receptive to questions and general communications as well!"
Dugway Hideaway Walking Distance to Lime Rock Park
Modern Copake Falls Getaway
Exterior

Modern Copake Falls Getaway

9.6 out of 10, Exceptional, (31)
"Cozy modern apartment with great views. Very close to Catamount and a short drive to Great Barrington. Michael was a great host."
Modern Copake Falls Getaway
Farmhouse-Loft -48 Main Street, Lenox, MA
Fridge, microwave, oven, stovetop

Farmhouse-Loft -48 Main Street, Lenox, MA

10.0 out of 10, Exceptional, (12)
"We had a bit of trouble with internet in the area so make sure you screenshot your instructions beforehand. The stay itself was lovely and the home was immaculate but cozy. We came on a super snowy/icy day and we messaged John about the icy roads outside and within 10 minutes, we got a phone call back and someone came to shovel and salt! There was also a cute coffee shop and tons of cute shops nearby. It was a perfect stay for our ski trip with our two girls. We will definitely recommend and...
Farmhouse-Loft -48 Main Street, Lenox, MA
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

Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (86)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored
Guesthouse Cabin vacation rentals in Berkshire County
Exterior

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 1,895
SAR 3,256 total
includes taxes & fees
11 Mar - 12 Mar
Guesthouse Cabin vacation rentals in Berkshire County
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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?
Here are some of the more popular apartments in the area: Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts: Includes Smart TVs. Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located 5.9 mi/9.6 km away in Great Barrington. Free WiFi, separate dining areas, and Smart TVs are included. The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock: It’s situated in Winsted, 19.1 mi/30.8 km away. Includes free WiFi, private patios, and private yards. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: 14.7 mi/23.6 km away in Lee. Private patios and fireplaces are included. 1500 sqft private entrance with beautiful views of the Berkshire Mountains: It’s located in Lee, 13.9 mi/22.4 km from Sheffield. Includes free WiFi, private patios, 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 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 Thom Reed UFO Monument Park 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.