Find hotels in Cheshire, MA from ฿2,395

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25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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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)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
United States
alton
The price is ฿6,682
฿7,063 total
includes taxes & fees
8 Jan - 9 Jan 2026
Harbour House Inn
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, (1000)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is ฿3,887
฿4,341 total
includes taxes & fees
25 Jan - 26 Jan 2026
Hotel Downstreet, an Ascend Collection Hotel
Suite, 2 Bedrooms | Frette Italian sheets, premium bedding, down duvets, minibar
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, (449)
"It is the perfect place to stay!"
United States
Darrell
The price is ฿4,727
฿5,974 total
includes taxes & fees
8 Jan - 9 Jan 2026
The Porches Inn at Mass MoCA
Single Room | In-room safe, desk, free WiFi, bed sheets
Blue Vista Motor Lodge

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (197)
"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 ฿5,550
฿5,866 total
includes taxes & fees
28 Dec - 29 Dec
Blue Vista Motor Lodge
Outdoor pool
Berkshire Travel Lodge

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (460)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is ฿2,127
฿2,383 total
includes taxes & fees
28 Dec - 29 Dec
Berkshire Travel Lodge
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel

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, (143)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is ฿5,400
฿6,031 total
includes taxes & fees
26 Dec - 27 Dec
The Trail in Adams - Berkshires’ Art Hotel
Romantic Room, 1 King Bed (Room 4) | Desk, iron/ironing board, free WiFi
The Revival House

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (25)
"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 ฿4,664
฿5,209 total
includes taxes & fees
29 Dec - 30 Dec
The Revival House
Front of property
Becket Motel

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60)
"Comfortable stay "
United States
Paul
The price is ฿3,014
฿4,409 total
includes taxes & fees
26 Dec - 27 Dec
Becket Motel
Lobby sitting area
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, (68)
"Extremely impressed by this hotel. The staff was very friendly and professional. The rooms were so comfortable and high quality everything! Check in and check out was easy. Highly recommend!"
United States
Jeanne
The price is ฿3,513
฿3,924 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (347)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ฿2,921
฿3,263 total
includes taxes & fees
28 Dec - 29 Dec
The Central Downtown Inn & Suites
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (811)
"Room spotless and staff helpful."
United States
William
The price is ฿2,489
฿2,781 total
includes taxes & fees
8 Jan - 9 Jan 2026
FairBridge Inn Express
Exterior
Hampton Terrace Inn

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is ฿6,803
฿7,599 total
includes taxes & fees
9 Jan - 10 Jan 2026
Hampton Terrace Inn
Front of property
Gregory House Country Inn

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (85)
"Loved the fact that we could have dinner and Sunday brunch right there."
United States
Maureen
The price is ฿3,499
฿3,884 total
includes taxes & fees
26 Dec - 27 Dec
Gregory House Country Inn
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"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 ฿2,672
฿2,985 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Inn
Lobby sitting area
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)
"Very friendly and good Breakfast."
United States
Jesse
The price is ฿2,374
฿2,651 total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Front of property
Blooming Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (125)
"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
United States
Allison
The price is ฿2,100
฿3,870 total
includes taxes & fees
7 Jan - 8 Jan 2026
Blooming Inn
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is ฿3,974
฿4,439 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Lenox Pittsfield
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (795)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is ฿3,067
฿4,120 total
includes taxes & fees
12 Jan - 13 Jan 2026
Berkshire Mountain Lodge
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is ฿12,439
฿13,894 total
includes taxes & fees
18 Jan - 19 Jan 2026
33 Main
Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm 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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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 Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

10/10 Excellent
"very good stay my only recommendation would be to have more coffee supplies as their is only enough for one pot of coffee and we were staying two days other than that very peaceful and comfortable."
Dennis 2-night trip
Posted 3 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap stays in Cheshire

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA
The price is ฿2,374 per night from 4 Jan to 5 Jan
฿2,374
฿2,651 total
4 Jan - 5 Jan 2026
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)

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 traveller data. Two other choices for your trip to the area are The Williams Inn and Holiday Inn & Suites Pittsfield-Berkshires by IHG. 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 room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.
What's the best LGBTQ-friendly place to stay 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. Holiday Inn & Suites Pittsfield-Berkshires by IHG and The Yankee, Trademark Collection by Wyndham are two additional hotels that feature an on-site pool. View all hotels with pools in Cheshire.
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 5 hotels and other accommodation options to choose from. Find out more about Cheshire.
What is there to see in Cheshire?
A favourite place to visit is Mount Greylock State Reservation. You'll also find Mount Greylock State Reservation Visitor Center and Mount Greylock in the area. Take a look at what more there is to see and do in Expedia's Cheshire guide.
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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