Photo by Ed Gaffny

Cheshire Hotels

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jul 7 - Jul 8
Tomorrow
Jul 8 - Jul 9
This weekend
Jul 11 - Jul 13
Next weekend
Jul 18 - Jul 20

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Cheshire hotels

Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (50)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is P14,801
P15,644 total
includes taxes & fees
Jul 8 - Jul 9
Harbour House Inn
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (549)
"Very clean and very nice staff. Breakfast was great"
The price is P8,873
P9,911 total
includes taxes & fees
Jul 31 - Aug 1
Berkshire Valley Inn
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (565)
"The staff, room and property was wonderful! "
The price is P7,843
P8,761 total
includes taxes & fees
Jul 9 - Jul 10
Maple Terrace Motel
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (354)
"The staff was friendly. Breakfast was diverse. Definitely would come back. The hot pool was a plus."
The price is P12,639
P14,118 total
includes taxes & fees
Jul 8 - Jul 9
Fairfield Inn & Suites by Marriott Williamstown
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (101)
"Great Place to stay in Small town"
The price is P4,977
P7,760 total
includes taxes & fees
Jul 9 - Jul 10
Blooming Inn
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (485)
"Had a fantastic stay, love this property. Cant wsit to go back"
The price is P9,855
P11,008 total
includes taxes & fees
Jul 15 - Jul 16
The Constance by the Lenox Collection
Cozy Corner Motel
Gazebo

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (831)
"Very, very clean with friendly owners. Located within a few minutes' drive of good restaurants and outdoor recreation areas. We would definitely stay again!"
The price is P5,360
P6,290 total
includes taxes & fees
Jul 8 - Jul 9
Cozy Corner Motel
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1006)
"Great place to stay "
The price is P6,667
P7,447 total
includes taxes & fees
Jul 13 - Jul 14
Best Western Plus Berkshire Hills Inn & Suites
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1005)
"Nice place to stay. Good breakfast. "
The price is P9,065
P10,125 total
includes taxes & fees
Jul 14 - Jul 15
The Yankee, Trademark Collection by Wyndham
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (395)
"Beautiful and peaceful property. Perfect for our last minute mother daughter get away. The staff was friendly and helpful. "
The price is P11,943
P14,600 total
includes taxes & fees
Aug 5 - Aug 6
The Porches Inn at Mass MoCA
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"I had excellent stay at the Red Lion Inn "
The price is P12,357
P16,324 total
includes taxes & fees
Aug 4 - Aug 5
The Red Lion Inn
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (294)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is P6,715
P7,500 total
includes taxes & fees
Jul 14 - Jul 15
The Central Downtown Inn & Suites
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1004)
"Fantastic place"
The price is P8,106
P9,054 total
includes taxes & fees
Aug 5 - Aug 6
Hotel Downstreet, Ascend Hotel Collection
The Springs Motel
Courtyard

The Springs Motel

2.0 star property
9.0 out of 10, Wonderful, (48)
"Adorable and immaculately clean. This is a super fun aesthetic place to stay. Add a vending machine or two or better - a lobby attendant that stays til 11 and it'll be perfect!! The pool is iconic. "
The price is P7,333
P8,044 total
includes taxes & fees
Jul 8 - Jul 9
The Springs Motel
Gregory House Country Inn
Bar (on property)

Gregory House Country Inn

3.0 star property
9.0 out of 10, Wonderful, (40)
"Wonderful stay and the food is excellent"
The price is P6,348
P7,046 total
includes taxes & fees
Jul 8 - Jul 9
Gregory House Country Inn
Blue Vista Motor Lodge
1 bedroom, in-room safe, desk, free WiFi

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (174)
"Lovely stay!"
The price is P11,866
P12,542 total
includes taxes & fees
Jul 8 - Jul 9
Blue Vista Motor Lodge
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (666)
"We love this place. It's a wonderful location in the Berkshires, easy to get to all of the surrounding towns and attractions. The amenities are awesome, the units are spotless, and the service is friendly and prompt. Have stayed twice and cannot wait to return again!"
The price is P8,916
P10,746 total
includes taxes & fees
Jul 10 - Jul 11
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (559)
"The hotel is very clean, well-managed, and quiet, and it's conveniently located near Tanglewood and other attractions. The room is clean, and the staff are all extremely kind and attentive to our needs (special thanks to Tapan!) We will definitely be coming back!"
The price is P11,962
P13,362 total
includes taxes & fees
Jul 13 - Jul 14
Courtyard by Marriott Lenox Berkshires
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (127)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
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
Sign in
Sign up, it's free

Family-friendly hotels in Cheshire you'll enjoy

Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (605)
The price is P3,597
P4,018 total
includes taxes & fees
Aug 3 - Aug 4
Econo Lodge Lee - Great Barrington
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.

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and wildlife.

See all hotels in Cheshire
Photo by Ed Gaffny
Open Photo by Ed Gaffny

Frequently asked questions

What's the best place to stay in Cheshire?

Located 9.8 mi (15.8 km) from the heart of Cheshire, Hotel Downstreet, Ascend Hotel Collection 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 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.

Where can I learn more about changing or cancelling my trip to Cheshire?

To find more details about updating your trip to Cheshire or cancelling it, click here.

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 is the best hotel near Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

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 3 hotels and other accommodations to choose from. Find out more about Cheshire.

What are the top places to visit in Cheshire?

A couple of favorite places to visit are Mount Greylock State Reservation and St Mary's of the Assumption Church. 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.