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30 Jul - 31 Jul
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Top 10 Cheshire hotels and places to stay

Huttopia Berkshires
Deluxe Tent | 2 bedrooms

Huttopia Berkshires

1.0 star property
The price is ฿3,955
฿4,418 total
includes taxes & fees
24 Aug - 25 Aug
Huttopia Berkshires
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (106)
"Lovely Inn and very responsive and approachable staff. "
The price is ฿3,064
฿4,686 total
includes taxes & fees
20 Aug - 21 Aug
Blooming Inn
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (725)
"Great quiet stay. "
The price is ฿3,209
฿3,585 total
includes taxes & fees
3 Aug - 4 Aug
The Villager Motel
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 ฿8,504
฿8,988 total
includes taxes & fees
5 Aug - 6 Aug
Harbour House Inn
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (653)
"It's a clean, nice place. And easy to get to the surrounding towns."
Berkshires Untold
The Revival House
Romantic Room, 1 King Bed (Room 4) | 1 bedroom, desk, iron/ironing board, free WiFi

The Revival House

3.0 star property
9.6 out of 10, Exceptional, (7)
"Beautifully renovated historical bed and breakfast that offers historical details along with modern touches. Our room was spacious and very clean and common areas are appointed with great attention to detail. "
The price is ฿5,835
฿6,518 total
includes taxes & fees
31 Jul - 1 Aug
The Revival House
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (58)
"Comfortable stay "
The price is ฿3,080
฿4,527 total
includes taxes & fees
3 Aug - 4 Aug
Becket Motel
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (932)
"Breakfast had lots of fresh fruit. Staff was very friendly and helpful. "
The price is ฿3,180
฿3,552 total
includes taxes & fees
12 Aug - 13 Aug
Willows Motel Williamstown
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, (1002)
"Clean,friendly staff and great location."
The price is ฿5,514
฿6,160 total
includes taxes & fees
3 Aug - 4 Aug
Hotel Downstreet, Ascend Hotel Collection
The Springs Motel
Courtyard

The Springs Motel

2.0 star property
9.0 out of 10, Wonderful, (52)
"Love this renovated motel. They made it cute and trendy"
The price is ฿4,064
฿4,458 total
includes taxes & fees
4 Aug - 5 Aug
The Springs Motel
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (771)
"Was great loved the jacuzzi tub "
The price is ฿3,209
฿3,585 total
includes taxes & fees
31 Jul - 1 Aug
Howard Johnson by Wyndham Lenox
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, (1000)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is ฿4,321
฿6,094 total
includes taxes & fees
27 Aug - 28 Aug
The Cornell Inn, Lenox & The Berkshires
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (534)
"Excellent stay!"
The price is ฿3,397
฿4,518 total
includes taxes & fees
17 Aug - 18 Aug
Berkshire Mountain Lodge
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (567)
"The staff, room and property was wonderful! "
The price is ฿3,647
฿4,074 total
includes taxes & fees
17 Aug - 18 Aug
Maple Terrace Motel
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (4)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is ฿5,155
฿5,758 total
includes taxes & fees
31 Jul - 1 Aug
Holiday Inn Express & Suites Pittsfield - Berkshires
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (837)
"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 ฿3,372
฿3,948 total
includes taxes & fees
6 Aug - 7 Aug
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, (1018)
"Very nice stay"
The price is ฿4,381
฿4,894 total
includes taxes & fees
17 Aug - 18 Aug
Best Western Plus Berkshire Hills Inn & Suites
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (615)
"It was a clean, well-run, low cost option. "
The price is ฿2,067
฿2,309 total
includes taxes & fees
13 Aug - 14 Aug
Econo Lodge Lee - Great Barrington
Blue Vista Motor Lodge
Single Room | 1 bedroom, in-room safe, desk, free WiFi

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (179)
"Clean, beautiful view wonderful service"
The price is ฿7,845
฿8,292 total
includes taxes & fees
4 Aug - 5 Aug
Blue Vista Motor Lodge
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

Top Cheshire Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"The property was spacious but still had a cozy feel. "
Marcella 1-night trip
Posted 2 days ago
The Williams Inn

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 Hotel Downstreet, Ascend Hotel Collection. 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.