Find hotels in Cheshire, MA from 1.857.793 ₫

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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 6.680.682 ₫
7.061.481 ₫ total
includes taxes & fees
27 Apr - 28 Apr
Harbour House Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (908 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is 2.369.970 ₫
2.647.257 ₫ total
includes taxes & fees
23 Apr - 24 Apr
Berkshires Untold

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)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
The price is 2.677.539 ₫
2.990.812 ₫ total
includes taxes & fees
23 Apr - 24 Apr
Best Western Plus Berkshire Hills Inn & Suites

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is 3.001.962 ₫
3.293.152 ₫ total
includes taxes & fees
5 May - 6 May
Shaker Mill Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
The price is 2.796.565 ₫
4.414.080 ₫ total
includes taxes & fees
22 Apr - 23 Apr
Blooming Inn

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 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 3.952.057 ₫
4.414.201 ₫ total
includes taxes & fees
22 Apr - 23 Apr
The Revival House

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,002 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is 2.663.583 ₫
2.975.222 ₫ total
includes taxes & fees
5 May - 6 May
Quality Inn Lee - Lenox South

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (911 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is 2.165.560 ₫
3.007.210 ₫ total
includes taxes & fees
27 Apr - 28 Apr
Berkshire Mountain Lodge

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (240 reviews)
"Found dead flies in the beds and the sheets were stained. I would not expect much from an inexpensive room but I do expect it to be clean."
United States
Heidi
The price is 2.014.475 ₫
2.250.168 ₫ total
includes taxes & fees
28 Apr - 29 Apr
Rodeway Inn

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (899 reviews)
"We love Cozy Corner. It's a snug, safe, well-maintained, home away from home. Love the ample breakfast and the genuine welcome we receive every time."
United States
Ann
The price is 2.085.574 ₫
2.457.923 ₫ total
includes taxes & fees
26 Apr - 27 Apr
Cozy Corner Motel

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is 3.012.495 ₫
3.364.957 ₫ total
includes taxes & fees
23 Apr - 24 Apr
The Yankee Inn

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is 3.976.283 ₫
4.441.508 ₫ total
includes taxes & fees
27 Apr - 28 Apr
Element Lenox Berkshires

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is 1.872.276 ₫
2.053.887 ₫ total
includes taxes & fees
22 Apr - 23 Apr
Pleasant Valley Motel West Stockbridge

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
The price is 5.332.432 ₫
5.636.381 ₫ total
includes taxes & fees
22 Apr - 23 Apr
UU Rowe Camp and Conference Center

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (785 reviews)
"very clean, up to day, no thrills overnighter. perfect stop from NYC to VT skiing"
United States
Martin
The price is 2.080.307 ₫
2.323.624 ₫ total
includes taxes & fees
26 Apr - 27 Apr
The Villager Motel

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (90 reviews)
"New hotel clean and nice. Heated pool and hot tub a bonus. Timely breakfast for early departures- great on demand coffee. Added bonus they have a car charger."
United States
Charline
The price is 3.107.294 ₫
3.470.953 ₫ total
includes taxes & fees
30 Apr - 1 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (851 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is 2.080.307 ₫
2.323.624 ₫ total
includes taxes & fees
22 Apr - 23 Apr
Howard Johnson by Wyndham Lenox

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,000 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is 2.896.630 ₫
3.235.536 ₫ total
includes taxes & fees
28 Apr - 29 Apr
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,000 reviews)
"Clean and cozy room, friendly staff, and fresh fruit for breakfast. Great location right next to Williams College."
United States
Phebe
The price is 2.126.390 ₫
2.375.237 ₫ total
includes taxes & fees
26 Apr - 27 Apr
Willows Motel Williamstown

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (600 reviews)
"Staff is very nice and the rooms are always clean!"
United States
Peter
The price is 2.739.048 ₫
3.059.569 ₫ total
includes taxes & fees
27 Apr - 28 Apr
Maple Terrace Motel
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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Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking and local cuisine.

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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