Photo by Ed Gaffny

Cheshire Hotels

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Aug 21 - Aug 22
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Aug 22 - Aug 23
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Aug 22 - Aug 24
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Top 10 trending Cheshire hotels

Our top choices for Cheshire hotels

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 P14,981
P15,835 total
includes taxes & fees
Aug 25 - Aug 26
Harbour House 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, (1000)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is P7,217
P8,061 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1010)
"Wonderful place to stay"
The price is P7,128
P7,963 total
includes taxes & fees
Sep 21 - Sep 22
The Yankee, Trademark Collection by Wyndham
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (688)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is P9,110
P10,176 total
includes taxes & fees
Aug 26 - Aug 27
Berkshires Untold
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1961)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is P6,172
P7,519 total
includes taxes & fees
Sep 1 - Sep 2
Vacation Village in the Berkshires
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, (1000)
"Great location!"
The price is P8,667
P9,681 total
includes taxes & fees
Aug 26 - Aug 27
Hotel Downstreet, Ascend Hotel Collection
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (523)
"Great place , love it, will return"
The price is P8,617
P9,626 total
includes taxes & fees
Sep 9 - Sep 10
The Constance by the Lenox Collection
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)
"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 P7,275
P10,354 total
includes taxes & fees
Sep 1 - Sep 2
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, (698)
"Pleasant stay"
The price is P5,214
P6,620 total
includes taxes & fees
Sep 3 - Sep 4
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1008)
"Loved our visit"
The price is P10,770
P14,576 total
includes taxes & fees
Aug 26 - Aug 27
The Red Lion Inn
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (582)
"Amazing place to stay. Can’t wait to go again. "
The price is P3,749
P5,460 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Mountain Lodge
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (767)
"Close to our target event a plus"
The price is P4,051
P4,526 total
includes taxes & fees
Sep 15 - Sep 16
FairBridge Inn Express
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, (863)
"Consistently a clean room with welcoming staff."
The price is P6,211
P6,938 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (19)
"Really enjoyed my stay here, definitely need a car to get around"
The price is P7,701
P8,602 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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, (625)
"It was lovely!"
The price is P3,633
P4,058 total
includes taxes & fees
Sep 3 - Sep 4
Econo Lodge Lee - Great Barrington
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (435)
"Property is close to Tanglewood Musical Venues. Parking is easy. The rooms are impeccably clean and the office manger was curteous."
The price is P3,846
P4,307 total
includes taxes & fees
Aug 28 - Aug 29
Berkshire Travel 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 P5,077
P5,671 total
includes taxes & fees
Sep 2 - Sep 3
Williamstown Motel
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (867)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is P6,267
P7,001 total
includes taxes & fees
Aug 25 - Aug 26
Howard Johnson by Wyndham Williamstown
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (728)
"Great quiet stay. "
The price is P5,071
P5,665 total
includes taxes & fees
Sep 14 - Sep 15
The Villager 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, (1003)
"Very clean rooms and excellent staff."
The price is P6,054
P6,762 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Berkshire Hills Inn & Suites
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

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"Great stay. Well balanced, clean, friendly. "
Derek 1-night trip
Posted 1 day ago
Hotel Downstreet, Ascend Hotel Collection

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 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 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 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.