Find hotels in Cheshire, MA from 1.685.928 ₫

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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 5.648.265 ₫
5.970.216 ₫ total
includes taxes & fees
26 Jan - 27 Jan
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 3.285.051 ₫
3.669.402 ₫ total
includes taxes & fees
2 Feb - 3 Feb
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, (197 reviews)
"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
United States
Jean
The price is 4.691.738 ₫
4.959.177 ₫ total
includes taxes & fees
19 Jan - 20 Jan
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 3.995.819 ₫
5.050.224 ₫ total
includes taxes & fees
20 Jan - 21 Jan
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 4.564.586 ₫
5.098.644 ₫ total
includes taxes & fees
19 Jan - 20 Jan
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 3.942.752 ₫
4.403.808 ₫ total
includes taxes & fees
19 Jan - 20 Jan
The Revival House

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 2.469.474 ₫
2.758.455 ₫ total
includes taxes & fees
26 Jan - 27 Jan
The Central Downtown Inn & Suites

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 3.219.634 ₫
3.596.331 ₫ total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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

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 2.104.307 ₫
2.350.511 ₫ total
includes taxes & fees
15 Feb - 16 Feb
FairBridge Inn Express

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 2.259.043 ₫
2.523.329 ₫ total
includes taxes & fees
26 Jan - 27 Jan
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, (1,001 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is 2.477.093 ₫
2.766.913 ₫ total
includes taxes & fees
26 Jan - 27 Jan
Best Western Plus Berkshire Hills Inn & Suites

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (661 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is 3.359.663 ₫
3.752.692 ₫ total
includes taxes & fees
23 Jan - 24 Jan
Hilton Garden Inn Lenox Pittsfield

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43 reviews)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is 5.750.941 ₫
6.423.767 ₫ total
includes taxes & fees
2 Feb - 3 Feb
Hampton Terrace Inn

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 11.165.600 ₫
12.248.795 ₫ total
includes taxes & fees
20 Jan - 21 Jan
Inn at Kenmore Hall

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 10.514.968 ₫
11.745.220 ₫ total
includes taxes & fees
18 Jan - 19 Jan
33 Main

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is 1.536.853 ₫
1.685.928 ₫ total
includes taxes & fees
25 Jan - 26 Jan
Pleasant Valley Motel West Stockbridge

Gateways Inn & Restaurant

Gateways Inn & Restaurant
3.0 star property
Lenox
8.0 out of 10, Very good, (197 reviews)
"Gateways Inn is a fantastic place to stay! The staff was very courteous and the room was spacious and very clean. The breakfast was included and very tasty. I highly suggest a stay there if you are planning on visiting the Berkshires!!!"
United States
Miguel
The price is 4.832.997 ₫
5.640.107 ₫ total
includes taxes & fees
30 Jan - 31 Jan
Gateways Inn & Restaurant

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 2.600.829 ₫
2.834.904 ₫ total
includes taxes & fees
23 Jan - 24 Jan
Starlight Inn

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 2.955.487 ₫
3.280.592 ₫ total
includes taxes & fees
30 Jan - 31 Jan
Gregory House Country Inn
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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An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

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Frequently asked questions

What's the seasonal weather in Cheshire?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

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