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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Sheffield apartments

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.6 out of 10, Excellent, (7 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is CA $128
CA $199 total
includes taxes & fees
Oct 12 - Oct 13
Cozy 1-bedroom studio in serene Great Barrington with AC
A sandy beach with a lake and forest in the background.

2. 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, (6 reviews)
"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"
United States
Marc R.
The price is CA $298
CA $468 total
includes taxes & fees
Oct 7 - Oct 8
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

3. 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 CA $214
CA $271 total
includes taxes & fees
Oct 7 - Oct 8
The Brooks Motel: Exceptional Suite
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

4. 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 CA $225
CA $284 total
includes taxes & fees
Oct 7 - Oct 8
The Brooks Motel: Exceptional Suite
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

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, (54 reviews)
"Clean property, very cute. Also very small. Cable/tv access was challenging, but all on all a good experience"
United States
traci
The price is CA $180
CA $338 total
includes taxes & fees
Oct 8 - Oct 9
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

6. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.2 out of 10, Wonderful, (5 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is CA $284
CA $539 total
includes taxes & fees
Oct 15 - Oct 16
Hudson NY’S Country Serenity Guest Suite.
A covered outdoor seating area with two chairs and a view of a grassy landscape.

7. 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 CA $321
CA $454 total
includes taxes & fees
Oct 8 - Oct 9
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

8. Urban Peak Escape, Lenox, MA

Urban Peak Escape, Lenox, MA
Lenox
8.0 out of 10, Very good, (1 review)
"Very nice. A few suggestions:- A higher end coffee maker would go a long way, or a latte machine. - Needs a toaster- Instructions on how to work the shower. We could only get the primary shower to work- A table and chairs (for eating a meal) would be good. Otherwise very comfortable and clean, and great location! "
United States
Nancy H.
The price is CA $545
CA $1,015 total
includes taxes & fees
Oct 12 - Oct 13
Urban Peak Escape, 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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Top Sheffield Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good
"I would recommend for families or large groups."
John 2-night trip
Posted 7 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

Find out more about Sheffield

Sheffield Apartments information

Number of reviews
32
Accommodation
54 Apartments
Lowest Price
CA $199
Highest Price
CA $1,015

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?
Below are some of the favorite apartments in the area to choose from: Cozy 1-bedroom studio in serene Great Barrington with AC: Located in Great Barrington, 5.6 mi/9.1 km from the heart of Sheffield. Includes free WiFi, private balconies, and Smart TVs. Access to onsite laundry facilities is available on site. Enjoy a restful stay with fast internet, smart TV and the company of your pet.: Located 19.5 mi/31.3 km away in Winsted. Free WiFi, private patios, and fireplaces are included. Access to a hot tub is available on site. Cozy 1-bedroom apartment in old farm house in historic South Lee: Located in South Lee, 12 mi/19.4 km away. Includes private patios. Access to onsite laundry facilities is available on site. 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. 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. Suter Farm and Lime Kiln Farm Wildlife Sanctuary 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.

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