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
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Sheffield apartments

Desk, iron/ironing board, WiFi, bed sheets

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 699 total
includes taxes & fees
13 Jul - 14 Jul
The Brooks Motel: Exceptional Suite
Pool

Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
8.8 out of 10, Excellent, (3 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is AED 823
AED 1,514 total
includes taxes & fees
14 Jul - 15 Jul
Hudson NY’S Country Serenity Guest Suite.
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very Good, (6 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 736 total
includes taxes & fees
13 Jul - 14 Jul
The Brooks Motel: Exceptional Suite
Smart TV, fireplace

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Great Barrington
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"The staff was absolutely friendly at all times. The coffee machine was nice to have available all day. The indoor pool, outdoor hot tub, and work out area were perfect. The space and kitchen in the suite were just right. My only critique would be that the AC unit was not sufficient. It blew mainly in the living room with one vent to the separate bedroom. That just didn’t keep the bedroom cold even with the unit set at 61."
Lindsay-Leigh 3-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

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. Access to onsite laundry facilities is available on site. Cozy 1-bedroom studio in serene Great Barrington with AC: Located 5.6 mi/9.1 km away in Great Barrington. Free WiFi, private balconies, and Smart TVs are included. 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. Magnolia Bluffs Casino and Bartholomew's Cobble 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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