Photo by Ed Gaffny

Cheshire Hotels from S$109

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Top 10 trending Cheshire hotels

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (52)
"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$359
includes taxes & fees
21 Oct - 22 Oct
Harbour House Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Great Indian restaurant in the hotel!"
The price is S$154
includes taxes & fees
2 Nov - 3 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (751)
"Easy parking, great community spaces, beautiful decor! "
The price is S$127
includes taxes & fees
2 Nov - 3 Nov
Berkshires Untold

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1003)
"Great location, very clean!"
The price is S$195
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2045)
"Easy check in and out, clean room. "
The price is S$147
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (894)
"Excellent customer service and great rooms"
The price is S$149
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1003)
"Decent value. On site restaurant is only open on weekends. "
The price is S$192
includes taxes & fees
10 Nov - 11 Nov
Hotel Downstreet, an Ascend Collection Hotel

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1005)
"Very friendly staff. "
The price is S$235
includes taxes & fees
28 Oct - 29 Oct
The Cornell Inn, Lenox & The Berkshires

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

3.5 star property
9.0 out of 10, Wonderful, (750)
"The lodging was convenient to all the area attractions."
The price is S$186
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (686)
"Great stay, perfect "
The price is S$140
includes taxes & fees
2 Nov - 3 Nov
Berkshire Mountain Lodge

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is S$142
includes taxes & fees
13 Oct - 14 Oct
Huttopia Berkshires

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1007)
"great place have stayed several times, and hope to return."
The price is S$261
includes taxes & fees
9 Nov - 10 Nov
The Red Lion Inn

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.4 out of 10, Exceptional, (52)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is S$172
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (778)
"Great property! Very large clean room in a unique hotel! "
The price is S$179
includes taxes & fees
3 Nov - 4 Nov
Hotel On North

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (519)
"Nice place to stay for a wedding "
The price is S$288
includes taxes & fees
2 Nov - 3 Nov
The Williams Inn

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (303)
"The rooms are dated but very clean and neat. This family run motel is convenient to everything in Williamstown and the university. The check-in was easy and staff were knowledgeable and kind."
The price is S$109
includes taxes & fees
9 Nov - 10 Nov
Williamstown Motel

The Constance by the Lenox Collection

3.5 star property
8.4 out of 10, Very good, (550)
"Very quiet and comfortable "
The price is S$166
includes taxes & fees
6 Nov - 7 Nov
The Constance by the Lenox Collection

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (425)
"Great hotel, lovely pool and hot tub. We got upgraded to a suite!"
The price is S$262
includes taxes & fees
10 Nov - 11 Nov
The Porches Inn at Mass MoCA

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1005)
"Great property would certainly stay again."
The price is S$147
includes taxes & fees
5 Nov - 6 Nov
Best Western Plus Berkshire Hills Inn & Suites

FairBridge Inn Express

2.5 star property
5.4 out of 10, (790)
"Good service and people"
The price is S$116
includes taxes & fees
23 Oct - 24 Oct
FairBridge Inn Express
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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Photo by Ed Gaffny
Open Photo by Ed Gaffny

Top Cheshire Hotel Reviews

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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 favourite place to visit is Mount Greylock State Reservation. 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.

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