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

Search Castles in Cheshire

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months
No exact matches found, but these alternatives could be just right

Recommended hotels in Cheshire

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 AU$371
includes taxes & fees
10 June - 11 June
Harbour House Inn

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, (1,001 reviews)
"Breakfast was reasonable. We had issue with our room and the staff helpfully moved us to another room. Would stay again"
United States
Anandaraja
The price is AU$183
includes taxes & fees
14 June - 15 June
Best Western Plus Berkshire Hills Inn & Suites

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,011 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is AU$176
includes taxes & fees
10 June - 11 June
The Yankee Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (461 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AU$213
includes taxes & fees
10 June - 11 June
Shaker Mill Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (137 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 AU$223
includes taxes & fees
10 June - 11 June
Blooming Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,005 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is AU$194
includes taxes & fees
14 June - 15 June
Quality Inn Lee - Lenox South

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!!"
United States
Grzegorz
The price is AU$200
includes taxes & fees
10 June - 11 June
Berkshire Lake Lodge

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (469 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
The price is AU$104
includes taxes & fees
11 June - 12 June
Berkshire Travel Lodge

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Cummington
10.0 out of 10, Exceptional, (2 reviews)
"We loved out stay! The lodge was simply magical. Our host was quite easy to connect with! We hope to visit again soon."
United States
Mary D.
The price is AU$195
includes taxes & fees
15 June - 16 June
Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.8 out of 10, Excellent, (5 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
The price is AU$178
includes taxes & fees
10 June - 11 June
Hideaway Inn Lenox

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (32 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is AU$242
includes taxes & fees
8 July - 9 July
The Revival House

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (981 reviews)
"Very nice hotel. Highly recommend the restaurant."
United States
Thomas
The price is AU$198
includes taxes & fees
11 June - 12 June
Berkshires Untold

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, (102 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is AU$214
includes taxes & fees
14 June - 15 June
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (912 reviews)
"Facilities were excellent. Staff was very helpful and very efficient & courteous in taking care of any concerns I had."
United States
Barbara J
The price is AU$141
includes taxes & fees
18 June - 19 June
Cozy Corner Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (611 reviews)
"Very well run property with good amenities and a lovely pool and sitting area. Lots of good attention to detail to make it a desirable place to stay!"
United States
Carolyn
The price is AU$182
includes taxes & fees
16 June - 17 June
Maple Terrace Motel

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,002 reviews)
"The property is in terrible condition."
United States
Olga V
The price is AU$112
includes taxes & fees
11 June - 12 June
Pleasant Valley Motel West Stockbridge

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (789 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is AU$141
includes taxes & fees
21 June - 22 June
The Villager Motel

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (246 reviews)
"Had a great stay."
United States
Trevor
The price is AU$114
includes taxes & fees
17 June - 18 June
Rodeway Inn

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (864 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is AU$125
includes taxes & fees
18 June - 19 June
Howard Johnson by Wyndham Lenox

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (971 reviews)
"Very quiet and clean will book again"
United States
Sade
The price is AU$225
includes taxes & fees
23 June - 24 June
Berkshire Mountain 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cheshire Hotel Reviews

Find out more about Cheshire

Cheshire Castles information

Number of reviews
11,929
Accommodation
1 Castles
Lowest Price
AU$104
Highest Price
AU$371

Explore a world of travel with Expedia