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Top 10 trending Cheshire hotels

Huttopia Berkshires
2 bedrooms

Huttopia Berkshires

1.0 star property
The price is P6,996
P7,815 total
includes taxes & fees
Aug 24 - Aug 25
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 P5,419
P8,290 total
includes taxes & fees
Aug 18 - Aug 19
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 P5,677
P6,342 total
includes taxes & fees
Aug 3 - Aug 4
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 P15,042
P15,900 total
includes taxes & fees
Aug 5 - Aug 6
Harbour House Inn
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (654)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is P32,465
P36,263 total
includes taxes & fees
Aug 8 - Aug 9
Berkshires Untold
The Revival House
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 P10,323
P11,530 total
includes taxes & fees
Aug 3 - Aug 4
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 P5,448
P8,007 total
includes taxes & fees
Aug 3 - Aug 4
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 P5,626
P6,284 total
includes taxes & fees
Aug 11 - Aug 12
Willows Motel Williamstown
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

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 P9,755
P10,896 total
includes taxes & fees
Aug 3 - Aug 4
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 P7,189
P7,886 total
includes taxes & fees
Aug 4 - Aug 5
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 P5,677
P6,342 total
includes taxes & fees
Aug 6 - Aug 7
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 P7,675
P10,824 total
includes taxes & fees
Aug 27 - Aug 28
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, (535)
"Excellent stay!"
The price is P6,009
P7,993 total
includes taxes & fees
Aug 17 - Aug 18
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 P6,452
P7,206 total
includes taxes & fees
Aug 17 - Aug 18
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 P10,188
P11,380 total
includes taxes & fees
Aug 6 - Aug 7
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 P5,964
P6,984 total
includes taxes & fees
Aug 11 - Aug 12
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, (1019)
"Very nice stay"
The price is P7,751
P8,657 total
includes taxes & fees
Aug 17 - Aug 18
Best Western Plus Berkshire Hills Inn & Suites
Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cribs/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 P3,656
P4,084 total
includes taxes & fees
Aug 13 - Aug 14
Econo Lodge Lee - Great Barrington
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, (179)
"Clean, beautiful view wonderful service"
The price is P13,878
P14,669 total
includes taxes & fees
Aug 5 - Aug 6
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Loved our visit"
Barbara 1-night trip
Posted 14 hours ago
The Red Lion 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 traveler data. This B&B offers free breakfast and free parking. Other good options for your stay in 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 hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.

Where can I learn more about changing or cancelling my trip to Cheshire?

To find more details about updating your trip to Cheshire or cancelling it, click here.

What is the favorite LGBTQ-friendly accommodation 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 the best hotel near Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

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 accommodations to choose from. Find out more about Cheshire.

What are the top places to visit in Cheshire?

A couple of favorite 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. Check out what more to see and do in Expedia's Cheshire guide.

What's the seasonal weather like in Cheshire?

The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.