Find hotels in Cheshire, MA from ₩94,630

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Our top choices for Cheshire hotels

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is ₩317,035
₩335,106 total
includes taxes & fees
Jan 21 - Jan 22
Harbour House Inn

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,000 reviews)
"Staff was pleasant and helpful, room spacey and all immaculate ."
United States
Barbara
The price is ₩185,134
₩206,794 total
includes taxes & fees
Feb 10 - Feb 11
Hotel Downstreet, an Ascend Collection Hotel

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (198 reviews)
"Great stay! "
United States
ALEKSey
The price is ₩263,172
₩278,173 total
includes taxes & fees
Feb 16 - Feb 17
Blue Vista Motor Lodge

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (452 reviews)
"It is the perfect place to stay!"
United States
Darrell
The price is ₩224,284
₩283,467 total
includes taxes & fees
Jan 21 - Jan 22
The Porches Inn at Mass MoCA

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (144 reviews)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is ₩256,208
₩286,184 total
includes taxes & fees
Jan 21 - Jan 22
The Trail in Adams - Berkshires’ Art Hotel

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (25 reviews)
"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
United States
melissa
The price is ₩221,305
₩247,184 total
includes taxes & fees
Jan 21 - Jan 22
The Revival House

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
Two Brooks Lodge

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (74 reviews)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is ₩187,714
₩209,676 total
includes taxes & fees
Jan 29 - Jan 30
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (354 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ₩138,519
₩154,729 total
includes taxes & fees
Feb 19 - Feb 20
The Central Downtown Inn & Suites

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (811 reviews)
"Room spotless and staff helpful."
United States
William
The price is ₩118,114
₩131,934 total
includes taxes & fees
Feb 3 - Feb 4
FairBridge Inn Express

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (87 reviews)
"Loved the fact that we could have dinner and Sunday brunch right there."
United States
Maureen
The price is ₩165,890
₩184,145 total
includes taxes & fees
Jan 21 - Jan 22
Gregory House Country Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (841 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is ₩126,716
₩141,541 total
includes taxes & fees
Feb 19 - Feb 20
Berkshire Inn

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,005 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is ₩138,947
₩155,204 total
includes taxes & fees
Jan 28 - Jan 29
Best Western Plus Berkshire Hills Inn & Suites

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is ₩619,324
₩691,785 total
includes taxes & fees
Jan 22 - Jan 23
33 Main

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is ₩847,884
₩930,136 total
includes taxes & fees
Jan 21 - Jan 22
Inn at Kenmore Hall

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (130 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is ₩132,712
₩220,493 total
includes taxes & fees
Jan 21 - Jan 22
Blooming Inn

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (663 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is ₩188,445
₩210,493 total
includes taxes & fees
Jan 23 - Jan 24
Hilton Garden Inn Lenox Pittsfield

Starlight Inn

Starlight Inn
2.0 star property
Bennington
6.8 out of 10, (223 reviews)
"Peaceful, quiet place to spend a night on the road."
United States
William
The price is ₩145,983
₩159,122 total
includes taxes & fees
Jan 21 - Jan 22
Starlight Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (443 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is ₩160,729
₩176,319 total
includes taxes & fees
Jan 21 - Jan 22
Shaker Mill Inn
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Stay near popular Cheshire attractions

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and natural setting.

An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Top Cheshire Hotel Reviews

More cheap stays in Cheshire

Frequently asked questions

What's the best place to stay in Cheshire?
Located 6.5 mi (10.5 km) from the heart of Cheshire, Vacation Village in the Berkshires is a top choice for your stay based on our traveler data. Other good options for your stay in the area are Berkshire Mountain Lodge and The Williams Inn. See all available top hotels, or vacation rentals in Cheshire.
If I need to cancel my hotel reservation in Cheshire, will I receive a refund?
Yes! Most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.
Where can I learn more about changing or cancelling my trip to Cheshire?
To find more details about updating your trip to Cheshire or cancelling it, click here.
What is the favorite LGBTQ-friendly accommodation in Cheshire?
Harbour House Inn is a top LGBTQ-friendly B&B, and features free breakfast and free WiFi. See all available hotels listed as LGBTQ-friendly in Cheshire.
What are some hotels with pools in Cheshire?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Berkshire Mountain Lodge and Holiday Inn & Suites Pittsfield-Berkshires by IHG are two additional hotels with an onsite pool. View all hotels with pools in Cheshire.
What is the best hotel near 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 is staying in Cheshire like?
Visitors can enjoy all that Cheshire has to offer including the ski areas, restaurants, and lake views. Tourists can also enjoy so much more including its shopping. In Cheshire, there are 6 hotels and other accommodations to choose from. Find out more about Cheshire.
What are the top places to visit in Cheshire?
A favorite place to visit is Mount Greylock State Reservation. You'll also find Mount Greylock State Reservation Visitor Center and Mount Greylock in the area. Check out what more to see and do in Expedia's Cheshire guide.
What's the seasonal weather like in Cheshire?
The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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