Cheshire Hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

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)
"Great place, great hosts, lovely experience. Would go back 100x. "
United States
Jared
The price is P14,680
P15,516 total
includes taxes & fees
Feb 24 - Feb 25
Harbour House Inn

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (200 reviews)
"Great stay! "
United States
ALEKSey
The price is P10,334
P10,923 total
includes taxes & fees
Mar 16 - Mar 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, (457 reviews)
"The great people!!!"
United States
Julie
The price is P8,312
P10,577 total
includes taxes & fees
Mar 22 - Mar 23
The Porches Inn at Mass MoCA

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (463 reviews)
"Nice location for my needs. Breakfast was not good or healthy. A little old, but had everything I needed. "
United States
Cameron
The price is P4,173
P4,673 total
includes taxes & fees
Feb 24 - Feb 25
Berkshire Travel Lodge

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)
"Spotless and front desk staff...friendly and accommodating "
United States
Barbara
The price is P6,596
P7,367 total
includes taxes & fees
Mar 22 - Mar 23
Hotel Downstreet, an Ascend Collection 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, (144 reviews)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is P10,054
P11,230 total
includes taxes & fees
Feb 20 - Feb 21
The Trail in Adams - Berkshires’ Art Hotel

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (26 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 P8,684
P9,699 total
includes taxes & fees
Feb 22 - Feb 23
The Revival House

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (357 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is P6,307
P7,045 total
includes taxes & fees
Mar 22 - Mar 23
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
9.2 out of 10, Wonderful, (82 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is P7,651
P8,546 total
includes taxes & fees
Mar 1 - Mar 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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 P4,635
P5,177 total
includes taxes & fees
Mar 8 - Mar 9
FairBridge Inn Express

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (843 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 P5,207
P5,816 total
includes taxes & fees
Feb 23 - Feb 24
Berkshire Inn

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 P13,019
P13,761 total
includes taxes & fees
Mar 5 - Mar 6
UU Rowe Camp and Conference Center

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 P33,327
P36,560 total
includes taxes & fees
Feb 20 - Feb 21
Inn at Kenmore Hall

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is P12,687
P14,172 total
includes taxes & fees
Feb 26 - Feb 27
Hampton Terrace 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, (1,002 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is P5,508
P6,153 total
includes taxes & fees
Feb 24 - Feb 25
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, (667 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is P7,932
P8,859 total
includes taxes & fees
Feb 27 - Feb 28
Hilton Garden Inn Lenox Pittsfield

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 P23,764
P26,544 total
includes taxes & fees
Feb 25 - Feb 26
33 Main

Starlight Inn

Starlight Inn
2.0 star property
Bennington
6.8 out of 10, (225 reviews)
"Peaceful, quiet place to spend a night on the road."
United States
William
The price is P5,728
P6,244 total
includes taxes & fees
Feb 22 - Feb 23
Starlight Inn

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 P3,391
P3,720 total
includes taxes & fees
Mar 3 - Mar 4
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 P10,900
P12,720 total
includes taxes & fees
Feb 22 - Feb 23
Gateways Inn & Restaurant
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Cheshire attractions

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.

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.
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 The Yankee, Trademark Collection by Wyndham are two additional hotels with an onsite 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 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.

Explore a world of travel with Expedia