Find hotels in Cheshire, MA from 2.019.210 ₫

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11 Dec - 12 Dec
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12 Dec - 13 Dec
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12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

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Our top choices for Cheshire hotels

Exterior
Harbour House Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is 5.666.755 ₫
5.989.892 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Harbour House Inn
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is 2.668.644 ₫
2.980.876 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1009)
"Great stay there!! Very friendly staff"
United States
Ann
The price is 1.972.476 ₫
2.203.256 ₫ total
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2168)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is 2.740.390 ₫
3.350.151 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Vacation Village in the Berkshires
Lobby lounge
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (813)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is 2.889.966 ₫
3.228.091 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Berkshires Untold
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (798)
"Place was great!"
United States
Benjamin
The price is 3.178.654 ₫
4.065.836 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (984)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is 2.443.294 ₫
2.729.160 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is 2.854.463 ₫
3.188.436 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is 3.981.870 ₫
5.626.040 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
The Red Lion Inn
Exterior
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is 4.404.106 ₫
5.066.967 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Cornell Inn, Lenox & The Berkshires
Check-in/check-out kiosk
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (787)
"This place is so peaceful and the staff is always helpful "
United States
Leona
The price is 2.601.040 ₫
3.494.177 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Berkshire Mountain Lodge
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1001)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is 2.824.227 ₫
3.154.662 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Hotel Downstreet, an Ascend Collection Hotel
Exterior
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (445)
"It is the perfect place to stay!"
United States
Darrell
The price is 4.008.900 ₫
5.066.756 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Porches Inn at Mass MoCA
Front of property
Chambery Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Property entrance
Hotel On North

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (805)
"Clean room and staff was super friendly"
United States
Yuen
The price is 3.927.193 ₫
4.386.675 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hotel On North
Front of property – evening/night
The Williams Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (548)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is 5.194.965 ₫
5.802.776 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Williams Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

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, (1001)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is 2.485.202 ₫
2.775.970 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Reception
The Villager Motel

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (764)
"It's very good for stay over"
United States
Frances
The price is 1.818.633 ₫
2.031.334 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Villager Motel
Property amenity
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
Williamstown
8.8 out of 10, Excellent, (394)
"our stay was great."
United States
nathaniel
The price is 4.138.049 ₫
4.622.201 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Fairfield Inn & Suites by Marriott Williamstown
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (589)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is 3.558.195 ₫
3.974.504 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Courtyard by Marriott Lenox Berkshires
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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Stay near popular Cheshire attractions

St Mary's of the Assumption Church

St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views or seek out its ski slopes.
See properties

Learn more about Cheshire

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

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

Top Cheshire Hotel Reviews

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent
"I visited Berkshire area for Thanksgiving and stayed at the brand new Holiday Inn Express. It was fantastic! The hotel is beautiful and pet friendly but also in a great location. The staff were amazing and professional. Over all 10/10 stay. Will definitely stay there again "
Kristina 2-night trip
Posted 13 days ago
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Huttopia Berkshires

Huttopia Berkshires

10/10 Excellent
"Healthy food too!"
GEORGINA 2-night trip
Posted 2 months ago
Huttopia Berkshires

More cheap stays in Cheshire

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA
The price is 1.972.476 ₫ per night from 24 Dec to 25 Dec
1.972.476 ₫
2.203.256 ₫ total
24 Dec - 25 Dec
includes taxes & fees
9/10 Wonderful! (1,008 reviews)

Hotels in Cheshire with star rating

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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