Photo by Ed Gaffny

Cheshire Hotels from S$102

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Check prices for these dates

Tonight
22 Jun - 23 Jun
Tomorrow
23 Jun - 24 Jun
Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 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, (49)
"Nice place for a weekend away."
The price is S$321
includes taxes & fees
26 Jun - 27 Jun
Harbour House Inn
The Revival House
1 bedroom, desk, iron/ironing board, free WiFi

The Revival House

3.0 star property
The price is S$242
includes taxes & fees
23 Jun - 24 Jun
The Revival House
The Trail in Adams - Berkshires’ Art Hotel
Garden

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (129)
"Stayed only one night Very cosy, quiet place "
The price is S$250
includes taxes & fees
23 Jun - 24 Jun
The Trail in Adams - Berkshires’ Art Hotel
The Springs Motel
Courtyard

The Springs Motel

2.0 star property
9.0 out of 10, Wonderful, (45)
"Springs Motel has a one of a kind vibe, loved the Double bed room! & managed by experienced, friendly people. Can’t wait to book a cabin next time with my family !! "
The price is S$188
includes taxes & fees
23 Jun - 24 Jun
The Springs Motel
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1832)
"second time stayed here. Love it!"
The price is S$164
includes taxes & fees
23 Jun - 24 Jun
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (933)
"Amazing place!"
The price is S$229
includes taxes & fees
25 Jun - 26 Jun
Jiminy Peak Mountain Resort
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (727)
"Friendly staff and quick checkin "
The price is S$102
includes taxes & fees
6 Jul - 7 Jul
FairBridge Inn Express
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (546)
"Very clean and very nice staff. Breakfast was great"
The price is S$213
includes taxes & fees
24 Jun - 25 Jun
Berkshire Valley Inn
Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (737)
"Best hotel in the Berkshire! "
The price is S$216
includes taxes & fees
30 Jun - 1 Jul
Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (796)
"Walking distance from the Colonial Theater, lots of dining options, good breakfast, comfortable bed, clean room, clean hotel."
The price is S$157
includes taxes & fees
26 Jun - 27 Jun
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (287)
"Very nice place to stay. Recently upgraded. Great location and convenient parking."
The price is S$185
includes taxes & fees
29 Jun - 30 Jun
The Central Downtown Inn & Suites
Berkshire Inn
1 bedroom, desk, iron/ironing board, free WiFi

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (774)
"The motel was nicely done and clean. The beds were comfortable "
The price is S$132
includes taxes & fees
23 Jun - 24 Jun
Berkshire Inn
1896 House Country Inn & Motels
Miscellaneous

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (417)
"Great"
1896 House Country Inn & Motels
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (845)
"Such nice people who run it. Nothing fancy but the people who work there are so friendly and accommodating "
The price is S$158
includes taxes & fees
23 Jun - 24 Jun
Howard Johnson by Wyndham Williamstown
Williamstown Motel
Reception

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (270)
"It was a very clean and the gentleman was so nice and spent a lot of time helping us figure out what to see and gave great suggestions on where to eat also. "
The price is S$122
includes taxes & fees
29 Jun - 30 Jun
Williamstown Motel
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, (1000)
"Staff super friendly, most comfortable beds imo I’ve slept in. I sleep better there then at my house."
The price is S$207
includes taxes & fees
21 Jul - 22 Jul
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (390)
"Phenomenal room, staff and location! We loved The Porches!!"
The price is S$312
includes taxes & fees
29 Jun - 30 Jun
The Porches Inn at Mass MoCA
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (348)
"It's a quick drive to Williams campus."
The price is S$229
includes taxes & fees
26 Jun - 27 Jun
Fairfield Inn & Suites by Marriott Williamstown
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (922)
"Clean, conscientious service, great breakast spread. "
The price is S$115
includes taxes & fees
23 Jun - 24 Jun
Willows Motel Williamstown
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (559)
"A great place to stay in Williamstown. Beautiful garden, friendly staff, very comfortable."
The price is S$165
includes taxes & fees
25 Jun - 26 Jun
Maple Terrace Motel
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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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

More cheap stays in Cheshire

More cheap stays in Cheshire

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, MA
The price is S$145 per night from 1 Jul to 2 Jul
S$145
1 Jul - 2 Jul
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)

Hotels near Cheshire Attractions

Hotels near Cheshire Attractions

Recent Reviews in Cheshire

Recent Reviews in Cheshire

The Williams Inn

The Williams Inn

5/5 Excellent
"great!"
A verified traveller from Fort Lauderdale stayed at The Williams Inn
Posted 2 days ago
The Williams Inn

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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, Trademark Collection by Wyndham is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Best Western Plus Berkshire Hills Inn & Suites and Vacation Village in the Berkshires. 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.