A lake surrounded by autumn-colored trees and hills.

Cheshire Hotels

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Check prices for these dates

This weekend
Jul 10 - Jul 12
Next weekend
Jul 17 - Jul 19

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Our top choices for Cheshire hotels

Motel
Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (55 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is P15,587
P16,475 total
includes taxes & fees
Jul 9 - Jul 10
Harbour House Inn
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (486 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is P4,146
P4,644 total
includes taxes & fees
Jul 9 - Jul 10
Berkshire Travel Lodge
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, (1,004 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is P7,815
P8,729 total
includes taxes & fees
Jul 15 - Jul 16
Best Western Plus Berkshire Hills Inn & Suites
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (923 reviews)
"Very clean! Friendly staff! Will stop there again!"
United States
Theresa
The price is P5,418
P6,368 total
includes taxes & fees
Jul 12 - Jul 13
Cozy Corner Motel
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,009 reviews)
"Great place"
United States
Michelle
The price is P8,792
P9,820 total
includes taxes & fees
Jul 23 - Jul 24
Quality Inn Lee - Lenox South
Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
The price is P9,289
P10,376 total
includes taxes & fees
Jul 12 - Jul 13
The Yankee Inn
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,003 reviews)
"Spacious and clean room, great location, friendly staff"
United States
Theresa
The price is P10,451
P11,673 total
includes taxes & fees
Jul 20 - Jul 21
Hotel Downstreet, an Ascend Collection Hotel
Minibar, iron/ironing board, free WiFi, bed sheets

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (253 reviews)
"Liked that fact that they let your bring your pet."
United States
Andrew
The price is P4,921
P5,497 total
includes taxes & fees
Jul 14 - Jul 15
Rodeway Inn
Mountain view

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (918 reviews)
"clean; quiet; good breakfast; as advertised; easy check-in/check out; convenient parking; "
United States
Thomas
The price is P7,372
P8,235 total
includes taxes & fees
Jul 9 - Jul 10
Howard Johnson by Wyndham Williamstown
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (798 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is P6,082
P6,794 total
includes taxes & fees
Jul 9 - Jul 10
The Villager Motel
Children's activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
The price is P4,147
P4,549 total
includes taxes & fees
Jul 9 - Jul 10
Pleasant Valley Motel West Stockbridge
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (874 reviews)
"I really enjoyed my stay at the Berkshire Inn, it was safe, clean, and in a convenient part of Pittsfield. Parking was a breeze and I was comfortable in my room. I would definitely book again!"
United States
Hannah
The price is P5,529
P6,176 total
includes taxes & fees
Jul 14 - Jul 15
Berkshire Inn
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,006 reviews)
"Great value and excellent location"
United States
Truett
The price is P5,778
P6,454 total
includes taxes & fees
Jul 12 - Jul 13
Willows Motel Williamstown
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (675 reviews)
"Old facility, needs refresh throughout"
United States
Michelle
The price is P5,170
P5,775 total
includes taxes & fees
Aug 2 - Aug 3
Econo Lodge Lee - Great Barrington
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (140 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is P7,520
P11,410 total
includes taxes & fees
Jul 13 - Jul 14
Blooming Inn
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (847 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is P3,815
P4,262 total
includes taxes & fees
Jul 22 - Jul 23
FairBridge Inn Express
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (618 reviews)
"Adorable little place! Staff was incredible and the rooms were cute but the only downside was the rooms had an older home smell!"
United States
Stephanie
The price is P7,926
P8,853 total
includes taxes & fees
Jul 19 - Jul 20
Maple Terrace Motel
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (110 reviews)
"Wonderful stay! Our room was beautiful - clean and cozy. I had a drink at the outside bar - it was lovely. Highly recommend staying here. It’s a hidden gem."
United States
Michelle
The price is P6,912
P7,672 total
includes taxes & fees
Jul 10 - Jul 11
Gregory House Country Inn
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (881 reviews)
"Great place"
United States
Luciane
The price is P6,082
P6,794 total
includes taxes & fees
Jul 9 - Jul 10
Howard Johnson by Wyndham Lenox
View from property

Starlight Inn

Starlight Inn
2.0 star property
Bennington
6.8 out of 10, (226 reviews)
"Lovely area to be in"
United States
Jeremia
The price is P6,580
P7,172 total
includes taxes & fees
Jul 13 - Jul 14
Starlight 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

10.0/10 (1 review)
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 lake views.

See all hotels in Cheshire
A lake surrounded by autumn-colored trees and hills.

Top Cheshire Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Breakfast is great"
Beth 7-night trip
Posted less than an hour ago
Hampton Inn & Suites Berkshires-Lenox

More cheap stays in Cheshire

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
The price is P3,815 per night from Jul 22 to Jul 23
P3,815
P4,262 total
Jul 22 - Jul 23
includes taxes & fees
5.4/10 (847 reviews)

Frequently asked questions

What's the best place to stay in Cheshire?
Located 12.2 mi (19.6 km) from the heart of Cheshire, The Yankee Inn is a top choice for your stay based on our traveler data. Other good options for your stay in the area are Vacation Village in the Berkshires and Berkshire Mountain Lodge. 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?
The Yankee Inn: Features a seasonal outdoor pool, an indoor pool, and buffet. Vacation Village in the Berkshires and Berkshire Mountain Lodge 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?
The picturesque setting of Mount Greylock State Reservation and Cheshire Reservoir exemplify the area's natural beauty. 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.

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