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Compare 1,145 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, 1,013 reviews
"the staff was great. soled a small issue with our room instantly and gave us a upgrade "
The price is $127
$141 total
includes taxes & fees
Jun 18 - Jun 19
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, 891 reviews
"Always a great HISTORIC INN "
The price is $152
$193 total
includes taxes & fees
Jun 19 - Jun 20
The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, 480 reviews
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The price is $149
$176 total
includes taxes & fees
Jun 13 - Jun 14
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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Seven Hills Inn
4.0 star property
7.8 out of 10, Good, 467 reviews
"Great breakfast, amazing property, comfortable beds! Water in shower wasn’t hot, had to take a “warm-cold” fast shower but it didn’t matter. The view, the quiet, nature and siting areas made the stay perfect. Will come again!!"
Seven Hills Inn
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, 160 reviews
"The experience was great and the staff were personable, helpful and warm."
The price is $141
$165 total
includes taxes & fees
Jun 13 - Jun 14
Lakehouse Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, 652 reviews
"I loved the staff and the accommodations. I’d recommend this property. "
The price is $188
$210 total
includes taxes & fees
Jun 13 - Jun 14
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, 1,002 reviews
"The staff was very friendly and the breakfast was delicious. The outdoor areas were beautiful. The room was beautifully designed"
The price is $117
$137 total
includes taxes & fees
Jun 12 - Jun 13
The Cornell Inn, Lenox
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, 605 reviews
"Cozy little room, very clean and comfortable, close to amenities, would definitely stay here again!"
The price is $86
$96 total
includes taxes & fees
Jun 12 - Jun 13
Monument Mountain Motel
Apple Tree Inn
3.0 star property
8.2 out of 10, Very Good, 216 reviews
"Had an extremely quiet and comfortable visit for one night. Terrific host and owner. Would visit again... : )"
The price is $188
$210 total
includes taxes & fees
Jun 13 - Jun 14
Apple Tree Inn
Quality Inn
2.5 star property
8.2 out of 10, Very Good, 1,013 reviews
"Really clean and great staff"
The price is $104
$116 total
includes taxes & fees
Jun 17 - Jun 18
Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, 504 reviews
"Very nice place! Great pool and hot tub. A shower at the pool area would’ve been a nice addition to rinse off chlorine. Overall a great value for the money spent. "
The price is $131
$146 total
includes taxes & fees
Jun 17 - Jun 18
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, 356 reviews
"Really nice rooms!"
The price is $249
$278 total
includes taxes & fees
Jun 13 - Jun 14
Chambery Inn
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, 32 reviews
"Great and excellent. Breakfast is perfect. "
The price is $182
$209 total
includes taxes & fees
Jun 17 - Jun 18
Blackberry River Inn
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, 463 reviews
"No amenities but that didn’t matter to us. Just needed a clean and quiet place for the night. I would stay here again"
The price is $75
$84 total
includes taxes & fees
Jun 16 - Jun 17
Travelodge by Wyndham Great Barrington Berkshires
The Briarcliff Motel
3.0 star property
8.8 out of 10, Excellent, 386 reviews
"Great deal!"
The price is $114
$128 total
includes taxes & fees
Jun 12 - Jun 13
The Briarcliff Motel
The Ponds at Foxhollow by Capital Vacations
3.0 star property
8.6 out of 10, Excellent, 110 reviews
"Comfortable condo accommodations. Ample size, Workable kitchen. Comfortable bed. Lovely setting. And a community facility with a pool, workout equipment, and sauna too! Small but tangible complaint: outside lighting is very bright and shines into BR window. "
The Ponds at Foxhollow by Capital Vacations
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, 386 reviews
"Wonderful place to stay in western Massachusetts."
The price is $215
$236 total
includes taxes & fees
Jun 17 - Jun 18
Shaker Mill Inn
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, 514 reviews
"Good value"
The price is $70
$78 total
includes taxes & fees
Jun 16 - Jun 17
Econo Lodge Lee - Great Barrington
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, 326 reviews
"This spot is very cozy and we really enjoyed our brief stay here. The owners are very friendly and make a delicious, home style breakfast complete with eggs from their chickens. It’s on a main road but we couldn’t hear the traffic and we slept well. The rooms aren’t over the top in size or luxury, but it was comfortable and the shared bathroom wasn’t an issue at all as it was right across the hall and we never had to wait for other patrons in order to use it. Would return and recommend!"
The price is $105
$121 total
includes taxes & fees
Jun 12 - Jun 13
Locust Tree Bed and Breakfast LLC
The Lenox Collection
3.5 star property
8.8 out of 10, Excellent, 216 reviews
"Great stay!"
The price is $98
$109 total
includes taxes & fees
Jun 16 - Jun 17
The Lenox Collection
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See all available properties in Sheffield
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.

More cheap stays in Sheffield

Stay near popular Sheffield attractions

Sheffield Travel Info

Number of reviews
4,654
Accommodation
1,145 hotels
Highest price
$249
Lowest price
$70
Reasons to visit
Bash Bish Falls State Park, Umpachene Falls Park and Mount Everett State Reservation
Hotels with nearby casinos
2
Hotels with nearby historical attractions
2

Frequently asked questions

Where is the best place to stay in Sheffield?

Race Brook Lodge is one of the top choices for your stay based on our traveler data. This hotel offers 2 bars and a restaurant. Other good choices for your trip to the area are Life House Berkshires and The Yankee, Trademark Collection by Wyndham. See all available top hotels, or vacation rentals in Sheffield.

What are some of the best vacation home rentals that Sheffield has to offer?

Pristine Home In Becket Woods: This vacation home rental outside of Sheffield is located near skiing and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private yard, a spa tub, and a selection of books so you can immerse yourself in your vacation. See all vacation rentals in Sheffield.

If I need to cancel my hotel reservation in Sheffield, will I receive a refund?

Yes! The majority of hotel room reservations are refundable provided that you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.

Where can I learn more about changing or cancelling my trip to Sheffield?

To access more information about changing or cancelling your trip to Sheffield, go to https://www.expedia.com/service/.

What's the best place to stay near Ashley House?

Sheffield 1802 House is one of the top choices for your stay based on our traveler data, and this 3.5-star B&B offers free breakfast and free parking. It's located 3.2 mi (5.1 km) from Ashley House. Another good option is Locust Tree Bed and Breakfast, located 3.8 mi (6.2 km) away.

What about the best place to stay near Magnolia Bluffs Casino?

One of the top choices for your stay is Sheffield 1802 House, located 1.6 mi (2.6 km) from Magnolia Bluffs Casino, and this 3.5-star B&B offers free breakfast and free parking.

What are some accommodations with pools in Sheffield?

Race Brook Lodge : Features 2 bars, a seasonal outdoor pool, and free self parking. The Yankee, Trademark Collection by Wyndham and The Red Lion Inn are a couple of other choices that offer an onsite pool. View all hotels with pools in Sheffield.

What is the best accommodation for staying close to Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

What's it like staying in Sheffield?

Visitors can enjoy all that Sheffield has to offer including the casinos and local tours. In Sheffield, there are 30 hotels and other accommodations to choose from. Find out more about Sheffield.

What should I see while I'm in Sheffield?

Favorite places to visit include Magnolia Bluffs Casino, Housatonic River, and Thom Reed UFO Monument Park. A couple of additional sights to add to your agenda are Ashley House and Mount Everett State Reservation. Check out what more to see and do in Expedia's Sheffield guide.

What's the weather like 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.

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