An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

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Check prices for these dates

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul
In one month
24 Jul - 26 Jul
In two months
21 Aug - 23 Aug
No exact matches found, but these alternatives could be just right

Recommended hotels in Cheshire

Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is ₹21,842
₹23,087 total
includes taxes & fees
8 Jul - 9 Jul
Harbour House Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,000 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is ₹11,253
₹12,569 total
includes taxes & fees
30 Jun - 1 Jul
Best Western Plus Berkshire Hills Inn & Suites
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is ₹13,518
₹15,100 total
includes taxes & fees
7 Jul - 8 Jul
The Yankee Inn
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (831 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is ₹5,569
₹6,221 total
includes taxes & fees
12 Jul - 13 Jul
FairBridge Inn Express
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (140 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is ₹9,294
₹15,020 total
includes taxes & fees
30 Jun - 1 Jul
Blooming Inn
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (61 reviews)
"Comfortable stay "
United States
Paul
The price is ₹8,569
₹12,735 total
includes taxes & fees
28 Jun - 29 Jun
Becket Motel
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (866 reviews)
"I really enjoyed my stay at the Berkshire Inn, it was safe, clean, and in a convenient part of Pittsfield. Parking was a breeze and I was comfortable in my room. I would definitely book again!"
United States
Hannah
The price is ₹7,425
₹8,294 total
includes taxes & fees
30 Jun - 1 Jul
Berkshire Inn
Lake view

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!!"
United States
Grzegorz
The price is ₹13,698
₹15,300 total
includes taxes & fees
29 Jun - 30 Jun
Berkshire Lake Lodge
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (917 reviews)
"Very clean! Friendly staff! Will stop there again!"
United States
Theresa
The price is ₹8,326
₹9,787 total
includes taxes & fees
19 Jul - 20 Jul
Cozy Corner Motel
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (34 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is ₹15,633
₹17,463 total
includes taxes & fees
29 Jun - 30 Jun
The Revival House
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,000 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is ₹14,260
₹15,928 total
includes taxes & fees
27 Jul - 28 Jul
Quality Inn Lee - Lenox South
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"Clean room and breakfast"
United States
Raphael
The price is ₹14,245
₹20,130 total
includes taxes & fees
7 Jul - 8 Jul
The Red Lion Inn
Children’s activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"The property is in terrible condition."
United States
Olga V
The price is ₹7,137
₹7,829 total
includes taxes & fees
30 Jun - 1 Jul
Pleasant Valley Motel West Stockbridge
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (472 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is ₹6,371
₹7,136 total
includes taxes & fees
30 Jun - 1 Jul
Berkshire Travel Lodge
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (999 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
The price is ₹13,249
₹16,908 total
includes taxes & fees
26 Jul - 27 Jul
Berkshire Mountain Lodge
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (115 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is ₹16,143
₹18,032 total
includes taxes & fees
6 Jul - 7 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ₹17,698
₹19,414 total
includes taxes & fees
29 Jun - 30 Jun
Shaker Mill Inn
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (669 reviews)
"Decent place.friendly, quiet"
United States
William
The price is ₹8,434
₹9,421 total
includes taxes & fees
7 Jul - 8 Jul
Econo Lodge Lee - Great Barrington
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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Top Cheshire Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Best hotel breakfast I have had in a long time. The breakfast attendant kept items well stocked. She made sure that vacated tables were cleaned and ready for the next guests to enjoy their meal. The room was kept very clean. I really enjoyed the fresh pancakes that were made to order by a pancake machine! Also, the pool and hot tub were great. The area was kept clean and towels were well stocked. Our room was also very spacious and immaculate."
Helen 1-night trip
Posted 3 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Cheshire

Cheshire Resorts information

Number of reviews
10,621
Accommodation
1 Resorts
Lowest Price
₹6,221
Highest Price
₹23,087

Frequently asked questions

What is Cheshire like for a resort holiday?
You deserve a holiday, and a resort is just the place to find all the amenities and services you need for a relaxing time in Cheshire. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for an amazing pool, shopping possibilities or activities for the youngsters.
What's the best resort for my stay in Cheshire?
Our highest-rated resort near Cheshire: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 20.6 mi (33.2 km) from Cheshire. Has a sauna, a fitness centre and a terrace.
What can I do in Cheshire?
Mount Greylock State Reservation, St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center are a few interesting places to visit nearby. In the area, other attractions include Mount Greylock and Mountain Coaster.
What's the weather like 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.
What's the best way to get to and around Cheshire?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.5 mi (18.5 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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