Photo by Ed Gaffny

Cheshire Hotels

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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, (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 P15,179
P16,045 total
includes taxes & fees
Oct 6 - Oct 7
Harbour House Inn
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1003)
"Great Indian restaurant in the hotel!"
The price is P6,149
P6,868 total
includes taxes & fees
Nov 2 - Nov 3
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Nice area to visit "
The price is P7,760
P8,668 total
includes taxes & fees
Nov 2 - Nov 3
The Yankee, Trademark Collection by Wyndham
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (744)
"Great location and very clean. Beautifully decorated and the restaurant is amazing. Just wish it offered a free breakfast with the room. "
The price is P5,064
P5,656 total
includes taxes & fees
Nov 2 - Nov 3
Berkshires Untold
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2035)
"Really nice place at a reasonable price"
Vacation Village in the Berkshires
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, (890)
"Excellent customer service and great rooms"
The price is P5,961
P6,658 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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, (1003)
"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 P7,389
P10,516 total
includes taxes & fees
Oct 28 - Oct 29
The Cornell Inn, Lenox & The Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (747)
"The lodging was convenient to all the area attractions."
The price is P6,719
P8,313 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hotel Downstreet, an Ascend Collection Hotel
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1000)
"Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool"
The price is P8,362
P9,341 total
includes taxes & fees
Nov 5 - Nov 6
Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (671)
"Very convenient set up of both room and kitchen, resort very easy to navigate. "
The price is P5,394
P7,318 total
includes taxes & fees
Nov 2 - Nov 3
Berkshire Mountain Lodge
Huttopia Berkshires
Restaurant

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 P5,671
P6,335 total
includes taxes & fees
Oct 6 - Oct 7
Huttopia Berkshires
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1004)
"great place have stayed several times, and hope to return."
The price is P9,780
P13,510 total
includes taxes & fees
Nov 2 - Nov 3
The Red Lion Inn
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.4 out of 10, Exceptional, (50)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is P8,313
P9,286 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (512)
"Great hotel, staff and restaurant!"
The price is P12,248
P13,681 total
includes taxes & fees
Nov 2 - Nov 3
The Williams Inn
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (777)
"Great property! Very large clean room in a unique hotel! "
The price is P7,234
P8,080 total
includes taxes & fees
Nov 3 - Nov 4
Hotel On North
Williamstown Motel
Exterior detail

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 P4,572
P5,107 total
includes taxes & fees
Nov 2 - Nov 3
Williamstown Motel
The Constance by the Lenox Collection
Front of property

The Constance by the Lenox Collection

3.5 star property
8.4 out of 10, Very Good, (549)
"Staff was so friendly and helpful. The room was small and comfortable and the grounds were well kept. "
The price is P5,486
P6,127 total
includes taxes & fees
Nov 3 - Nov 4
The Constance by the Lenox Collection
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.6 out of 10, (884)
"All good except needs updating in rooms and add a microwave, more updated breakfast room needed."
The price is P6,365
P7,110 total
includes taxes & fees
Oct 6 - Oct 7
Howard Johnson by Wyndham Williamstown
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, (1000)
"Great property would certainly stay again."
The price is P5,884
P6,573 total
includes taxes & fees
Nov 2 - Nov 3
Best Western Plus Berkshire Hills Inn & Suites
The Porches Inn at Mass MoCA
2 bedrooms, Frette Italian sheets, premium bedding, down comforters

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 P11,264
P13,875 total
includes taxes & fees
Nov 5 - Nov 6
The Porches Inn at Mass MoCA
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 natural setting.

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

Top Cheshire Hotel Reviews

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent
"Bo at front desk was super nice, welcoming and polite. "
Daniel 1-night trip
Posted 14 hours ago
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

More cheap stays in Cheshire

More cheap stays in Cheshire

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is P4,572 per night from Oct 19 to Oct 20
P4,572
P5,106 total
Oct 19 - Oct 20
includes taxes & fees
7.4/10 Good! (802 reviews)

Frequently asked questions

What's the best place to stay in Cheshire?

Located 6.5 mi (10.5 km) from the heart of Cheshire, Vacation Village in the Berkshires is a top choice for your stay based on our traveler data. Other good options for your stay in the area are Berkshire Mountain Lodge and Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG. 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 4 hotels and other accommodations to choose from. Find out more about Cheshire.

What are the top places to visit in Cheshire?

A favorite place to visit is Mount Greylock State Reservation. 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.

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Explore a world of travel with Expedia