Cheshire hotels from HK$602

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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)
  • cleanliness
    Serene lakeside B&B near charming Adams Theatre with complimentary full breakfast.
"Nice place for a weekend away."
United States
Gregory
The price is HK$1,680
HK$1,776 total
includes taxes & fees
9 Feb - 10 Feb
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, (1,001 reviews)
"Room was cozy and clean. Staff was very responsive and courteous. The entire place was great from location to feel."
United States
Kelly
The price is HK$982
HK$1,097 total
includes taxes & fees
23 Feb - 24 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, (199 reviews)
  • cleanliness
    Relax at this mountain lodge with two hot tubs and a sauna after exploring North Adams.
"Great stay! "
United States
ALEKSey
The price is HK$1,395
HK$1,475 total
includes taxes & fees
9 Feb - 10 Feb
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, (454 reviews)
"The great people!!!"
United States
Julie
The price is HK$1,122
HK$1,428 total
includes taxes & fees
9 Mar - 10 Mar
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 HK$562
HK$630 total
includes taxes & fees
9 Feb - 10 Feb
Berkshire Travel Lodge

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)
  • cleanliness
    Take in art and nature steps from the Berkshires' best hiking trails and museums.
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is HK$1,358
HK$1,516 total
includes taxes & fees
9 Feb - 10 Feb
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)
  • cleanliness
    Serene getaway near Adams Theatre with daily self-serve breakfast included.
"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 HK$1,173
HK$1,310 total
includes taxes & fees
9 Feb - 10 Feb
The Revival House

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
  • cleanliness
    Wake up to tranquil woodland views at this Becket retreat near hiking trails.
"Comfortable stay "
United States
Paul
The price is HK$712
HK$1,058 total
includes taxes & fees
9 Feb - 10 Feb
Becket Motel

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
  • cleanliness
    Scenic Vermont retreat with hiking trails and modern comforts near museums.
"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

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, (81 reviews)
  • cleanliness
    Relax in the heart of the Berkshires with an indoor pool and hot tub after a day out.
"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 HK$1,032
HK$1,152 total
includes taxes & fees
26 Feb - 27 Feb
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (355 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is HK$875
HK$977 total
includes taxes & fees
22 Feb - 23 Feb
The Central Downtown Inn & Suites

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43 reviews)
  • cleanliness
    Historic elegance near Tanglewood with outdoor pool and tennis courts.
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is HK$1,710
HK$1,910 total
includes taxes & fees
9 Feb - 10 Feb
Hampton Terrace Inn

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (811 reviews)
  • cleanliness
    Enjoy tranquil lodging in Pittsfield with free WiFi and convenient parking.
"Room spotless and staff helpful."
United States
William
The price is HK$626
HK$699 total
includes taxes & fees
21 Feb - 22 Feb
FairBridge Inn Express

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (87 reviews)
  • cleanliness
    Enjoy a charming retreat near Pineridge Cross Country Ski Centre and Berkshire.
"Loved the fact that we could have dinner and Sunday brunch right there."
United States
Maureen
The price is HK$826
HK$917 total
includes taxes & fees
9 Feb - 10 Feb
Gregory House Country Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (842 reviews)
  • cleanliness
    Enjoy a tranquil stay near Tanglewood Music Centre with a refreshing pool.
"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 HK$672
HK$750 total
includes taxes & fees
9 Feb - 10 Feb
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)
  • cleanliness
    Tranquil Berkshire hideaway near Tanglewood with complimentary amenities.
"Very friendly and good Breakfast."
United States
Jesse
The price is HK$737
HK$823 total
includes taxes & fees
10 Feb - 11 Feb
Best Western Plus Berkshire Hills Inn & Suites

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
  • cleanliness
    Experience luxury in a Lenox B&B near the library and The Bookshop.
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is HK$3,107
HK$3,471 total
includes taxes & fees
23 Feb - 24 Feb
33 Main

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 HK$4,493
HK$4,928 total
includes taxes & fees
9 Feb - 10 Feb
Inn at Kenmore Hall

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
  • cleanliness
    Charming Berkshires B&B with outdoor pool near Tanglewood Music Centre.
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (130 reviews)
  • cleanliness
    Discover riverside charm in Shelburne Falls with free WiFi and winter activities.
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is HK$703
HK$1,168 total
includes taxes & fees
9 Feb - 10 Feb
Blooming 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

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 traveller data. Two other choices for your trip to the area are Berkshire Mountain Lodge and The Williams Inn. See all available top hotels, or vacation rentals in Cheshire.
What are some of the best holiday rentals that Cheshire has to offer?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Cheshire offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. See all 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. Berkshire Mountain Lodge and Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG 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 6 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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