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Cheshire Hotels from S$102

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24 Aug - 25 Aug
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25 Aug - 26 Aug
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29 Aug - 31 Aug
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Top 10 trending Cheshire hotels

The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (729)
"Great quiet stay. "
The price is S$127
includes taxes & fees
1 Sept - 2 Sept
The Villager Motel
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (3)
"Perfect place for a relaxing getaway! We loved everything! "
The price is S$140
includes taxes & fees
1 Sept - 2 Sept
Huttopia Berkshires
Element Lenox Berkshires
Lobby lounge

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is S$218
includes taxes & fees
1 Sept - 2 Sept
Element Lenox Berkshires
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"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$320
includes taxes & fees
9 Sept - 10 Sept
Harbour House Inn
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (110)
"Lovely Inn and very responsive and approachable staff. "
The price is S$203
includes taxes & fees
28 Aug - 29 Aug
Blooming Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is S$181
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (786)
"My stay was perfect. I can't wait to stay there again. "
The price is S$113
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Lenox
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (940)
"Comfortable, clean, and great continental breakfast options! "
The price is S$128
includes taxes & fees
1 Sept - 2 Sept
Willows Motel Williamstown
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (592)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge
Williamstown Motel
Exterior detail

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (290)
"Small comfortable room, accommodating staff, very close to Williams College."
The price is S$115
includes taxes & fees
11 Sept - 12 Sept
Williamstown Motel
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is S$233
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires
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, (1001)
"Very clean rooms and excellent staff."
The price is S$152
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Berkshire Hills Inn & Suites
The Porches Inn at Mass MoCA
2 bedrooms, Frette Italian sheets, premium bedding, down duvets

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (412)
"Great well managed property with a unique style and nice amenities. Also, a continental breakfast is included with the stay."
The price is S$283
includes taxes & fees
22 Sept - 23 Sept
The Porches Inn at Mass MoCA
The Springs Motel
Courtyard

The Springs Motel

2.0 star property
9.2 out of 10, Wonderful, (61)
"I was pleasantly surprised to find this gem in the middle of town. Relatively inexpensive for the area. Clean rooms and property. Nice staff. Beautiful pool. Would definitely recommend "
The price is S$175
includes taxes & fees
26 Aug - 27 Aug
The Springs Motel
Pleasant Valley Motel West Stockbridge
Garden view

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (997)
"Clean and convenient. Great value."
The price is S$98
includes taxes & fees
2 Sept - 3 Sept
Pleasant Valley Motel West Stockbridge
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (693)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is S$230
includes taxes & fees
1 Sept - 2 Sept
Berkshires Untold
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1004)
"Very comfortable and a nice breakfast "
The price is S$157
includes taxes & fees
8 Sept - 9 Sept
Quality Inn
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cots/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (23)
"Brand new hotel. Really nice staff. Great location to Tanglewood and great rates. "
The price is S$193
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (847)
"We thoroughly enjoyed our 1-night stay at the Cozy Corner! Rooms were very clean, and beds very comfortable! They also had a great breakfast, and I loved the outdoor seating area by the babbling brook!"
The price is S$141
includes taxes & fees
2 Sept - 3 Sept
Cozy Corner Motel
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (624)
"Convenient location for my trip"
The price is S$99
includes taxes & fees
26 Aug - 27 Aug
Wagon Wheel 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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Learn more about Cheshire

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

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

Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."
James 5-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Frequently asked questions

What's the best place to stay in Cheshire?

Harbour House Inn is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Two other choices for your trip to 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 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 4 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.