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Check prices for these dates

Tonight
11 Feb - 12 Feb
Tomorrow
12 Feb - 13 Feb
This weekend
13 Feb - 15 Feb
Next weekend
20 Feb - 22 Feb

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Our top choices for Cheshire hotels

Exterior

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 Rp3.613.075
Rp3.819.020 total
includes taxes & fees
18 Feb - 19 Feb
Harbour House Inn
Exterior

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (200 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 Rp3.001.205
Rp3.172.280 total
includes taxes & fees
16 Feb - 17 Feb
Blue Vista Motor Lodge
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains

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)
"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 Rp2.112.638
Rp2.359.816 total
includes taxes & fees
5 Mar - 6 Mar
Hotel Downstreet, an Ascend Collection Hotel
Exterior

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (455 reviews)
"The great people!!!"
United States
Julie
The price is Rp2.414.038
Rp3.071.905 total
includes taxes & fees
12 Mar - 13 Mar
The Porches Inn at Mass MoCA
Lobby sitting area

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 Rp1.209.792
Rp1.354.987 total
includes taxes & fees
15 Feb - 16 Feb
Berkshire Travel Lodge
Terrace/patio

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 Rp2.919.869
Rp3.261.495 total
includes taxes & fees
12 Feb - 13 Feb
The Trail in Adams - Berkshires’ Art Hotel
55-inch LCD TV with digital channels, printers

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 Rp2.522.094
Rp2.817.022 total
includes taxes & fees
12 Feb - 13 Feb
The Revival House
Indoor pool

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)
  • 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 Rp2.219.893
Rp2.479.623 total
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Terrace/patio

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 Rp1.832.399
Rp2.046.739 total
includes taxes & fees
12 Feb - 13 Feb
The Central Downtown Inn & Suites
Desk, iron/ironing board, free WiFi, bed sheets

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 Rp1.346.080
Rp1.503.572 total
includes taxes & fees
24 Feb - 25 Feb
FairBridge Inn Express
Exterior

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)
  • cleanliness
    Tranquil B&B with free breakfast in Rowe, hiking trails and WiFi for nature lovers.
"Yes"
United States
Stuart
The price is Rp3.781.125
Rp3.996.649 total
includes taxes & fees
22 Feb - 23 Feb
UU Rowe Camp and Conference Center
Seasonal outdoor pool

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 Rp1.445.062
Rp1.614.120 total
includes taxes & fees
18 Feb - 19 Feb
Berkshire 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
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Tranquil Berkshire hideaway near Tanglewood with complimentary amenities.
"Very friendly and good Breakfast."
United States
Jesse
The price is Rp1.613.112
Rp1.801.832 total
includes taxes & fees
10 Mar - 11 Mar
Best Western Plus Berkshire Hills Inn & Suites
Exterior detail

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 Rp3.678.615
Rp4.108.991 total
includes taxes & fees
12 Feb - 13 Feb
Hampton Terrace Inn
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (667 reviews)
  • cleanliness
    Perfect setting for a Berkshires visit with an indoor pool and Asian dining.
" Nice staff - beautiful hotel!"
United States
MARY
The price is Rp2.304.452
Rp2.573.932 total
includes taxes & fees
27 Feb - 28 Feb
Hilton Garden Inn Lenox Pittsfield
Lobby

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 Rp9.662.875
Rp10.600.258 total
includes taxes & fees
12 Feb - 13 Feb
Inn at Kenmore Hall
Exterior

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 Rp6.890.050
Rp7.696.186 total
includes taxes & fees
26 Feb - 27 Feb
33 Main
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (445 reviews)
  • cleanliness
    Enjoy a relaxing Berkshires retreat with free breakfast and parking amenities.
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is Rp2.050.210
Rp2.249.081 total
includes taxes & fees
22 Feb - 23 Feb
Shaker Mill Inn
Dining room

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 Rp1.890.562
Rp2.098.523 total
includes taxes & fees
12 Feb - 13 Feb
Gregory House Country Inn
Front of property

Gateways Inn & Restaurant

Gateways Inn & Restaurant
3.0 star property
Lenox
8.0 out of 10, Very good, (197 reviews)
  • cleanliness
    Luxurious Berkshires retreat with fine dining and historic charm in Lenox.
"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 Rp2.809.124
Rp3.278.248 total
includes taxes & fees
22 Feb - 23 Feb
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.
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Stay near popular Cheshire attractions

St Mary's of the Assumption Church

This historic Catholic parish has served Cheshire's community since 1879, offering a serene space for reflection. Visit during religious holidays to experience special services in its traditional architectural setting.
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

Element Lenox Berkshires

Element Lenox Berkshires

10/10 Excellent
"Awesome "
Manuel 1-night trip
Posted 3 weeks ago
Element Lenox Berkshires

More cheap stays in Cheshire

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is Rp1.159.545 per night from 18 Feb to 19 Feb
Rp1.159.545
Rp1.295.161 total
18 Feb - 19 Feb
includes taxes & fees
7.4/10 Good! (829 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 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 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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