Photo by Ed Gaffny

Cheshire Hotels from S$91

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Check prices for these dates

Tonight
6 Jul - 7 Jul
Tomorrow
7 Jul - 8 Jul
Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul

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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 S$318
includes taxes & fees
8 Jul - 9 Jul
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 S$224
includes taxes & fees
31 Jul - 1 Aug
Berkshire Valley Inn
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (564)
"The staff, room and property was wonderful! "
The price is S$198
includes taxes & fees
9 Jul - 10 Jul
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, (352)
"The staff was friendly. Breakfast was diverse. Definitely would come back. The hot pool was a plus."
The price is S$319
includes taxes & fees
7 Jul - 8 Jul
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 S$175
includes taxes & fees
9 Jul - 10 Jul
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 S$251
includes taxes & fees
14 Jul - 15 Jul
The Constance by the Lenox Collection
Cozy Corner Motel
Gazebo

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (829)
"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 S$142
includes taxes & fees
7 Jul - 8 Jul
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, (1005)
"Great place to stay "
The price is S$168
includes taxes & fees
13 Jul - 14 Jul
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, (1003)
"Nice place to stay. Good breakfast. "
The price is S$229
includes taxes & fees
13 Jul - 14 Jul
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, (394)
"Perfect for our needs"
The price is S$330
includes taxes & fees
4 Aug - 5 Aug
The Porches Inn at Mass MoCA
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"I had excellent stay at the Red Lion Inn "
The price is S$347
includes taxes & fees
4 Aug - 5 Aug
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 S$169
includes taxes & fees
14 Jul - 15 Jul
The Central Downtown Inn & Suites
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (367)
"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 curtains

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1004)
"Fantastic place"
The price is S$204
includes taxes & fees
4 Aug - 5 Aug
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 S$257
includes taxes & fees
21 Jul - 22 Jul
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 S$159
includes taxes & fees
7 Jul - 8 Jul
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 S$283
includes taxes & fees
7 Jul - 8 Jul
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, (665)
"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 S$237
includes taxes & fees
9 Jul - 10 Jul
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 S$302
includes taxes & fees
13 Jul - 14 Jul
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.
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Family-friendly hotels in Cheshire you'll enjoy

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

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (604)
The price is S$91
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Lee - Great Barrington

Hotels with a spa in Cheshire may fit your trip

Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (367)
Chambery 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.

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 traveller data. Two other choices for your trip to 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 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 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 accommodation options to choose from. Find out more about Cheshire.

What is there to see in Cheshire?

A couple of favourite 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. 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.