A lake surrounded by autumn-colored trees and hills.

Search Castles in Cheshire from CA $98

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Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29
No exact matches found, but these alternatives could be just right

Recommended hotels in Cheshire

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.6 out of 10, Exceptional, (57 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $359
CA $379 total
includes taxes & fees
Sep 29 - Sep 30
Harbour House Inn
A patio area with outdoor furniture, a fire pit, and potted plants.

2. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (120 reviews)
"Loved the vibe!"
United States
Elizabeth
The price is CA $161
CA $176 total
includes taxes & fees
Sep 30 - Oct 1
The Springs Motel
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,683 reviews)
"Love this place for a weekend getaway."
United States
Jacob
The price is CA $135
CA $166 total
includes taxes & fees
Sep 30 - Oct 1
Vacation Village in the Berkshires
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

4. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (911 reviews)
"Parking and staff were good"
United States
William
The price is CA $88
CA $98 total
includes taxes & fees
Sep 29 - Sep 30
FairBridge Inn Express
A single-story building with a porch, a chimney, and a satellite dish.

5. Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (276 reviews)
"Room was very clean and spacious. Front desk personnel were extremely friendly and helpful. Downside was proximity and noise from road. Made for a noisy night"
United States
Brandie
The price is CA $108
CA $121 total
includes taxes & fees
Oct 4 - Oct 5
Rodeway Inn
A hotel with a covered entrance, a registration desk, and a parking area.

6. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,014 reviews)
"The room was spacious, clean and comfortable. I will definitely stay there again."
United States
William
The price is CA $151
CA $169 total
includes taxes & fees
Sep 29 - Sep 30
The Yankee Inn
A two-story building with a symmetrical facade, large columns, and a central entrance.

7. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (38 reviews)
"Room 6 was much larger than expected! We arrived after hours and it was very easy to find our room."
United States
Katrina
The price is CA $234
CA $262 total
includes taxes & fees
Sep 29 - Sep 30
The Revival House
A modern hotel building with the name "Hotel Downtown" on the facade.

8. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,003 reviews)
"Clean room, great location. Perfect base for a weekend in the Berkshires."
United States
Alexandra
The price is CA $191
CA $213 total
includes taxes & fees
Oct 14 - Oct 15
Hotel Downstreet, an Ascend Collection Hotel
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

9. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,004 reviews)
"Friendly staff. Good location."
United States
Joe
The price is CA $150
CA $167 total
includes taxes & fees
Oct 18 - Oct 19
Best Western Plus Berkshire Hills Inn & Suites
A motel with a two-story structure, a covered parking area, and a well-maintained lawn with a flower bed.

10. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (954 reviews)
"Lovely classic motel with attentive staff. Owner lives on property and is very engaging. Lovely grounds."
United States
Jonathan
The price is CA $125
CA $147 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Corner Motel
A multi-story hotel with a prominent sign for Holiday Inn & Suites.

11. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,002 reviews)
"Look good for being under constructikn"
United States
Debra
The price is CA $157
CA $175 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A motel with multiple rooms, a parking area, and a large tree in the foreground.

12. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (947 reviews)
"Great place"
United States
Donna
The price is CA $132
CA $147 total
includes taxes & fees
Sep 29 - Sep 30
Howard Johnson by Wyndham Williamstown
A two-story wooden building with a porch, a sign reading "The Trail," and a small staircase leading to the entrance.

13. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (157 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is CA $247
CA $276 total
includes taxes & fees
Sep 29 - Sep 30
The Trail in Adams - Berkshires’ Art Hotel
A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

14. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (349 reviews)
"Excellent service, excellent stay."
United States
Ahmet
The price is CA $142
CA $158 total
includes taxes & fees
Sep 29 - Sep 30
Williamstown Motel
A motel with a parking lot, a swimming pool, and outdoor seating.

15. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (931 reviews)
"Very well maintained and clean for an older looking property. I stayed here twice now."
United States
Kristina
The price is CA $113
CA $126 total
includes taxes & fees
Oct 29 - Oct 30
Berkshire Inn
A white two-story building with a porch, labeled as a motel.

16. Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (1,003 reviews)
"The staff are what truly makes this property special. They are so nice and accomodating."
United States
Linda
The price is CA $146
CA $164 total
includes taxes & fees
Sep 29 - Sep 30
Willows Motel Williamstown
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

17. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (929 reviews)
"Very nice and reasonably priced hotel for the region."
United States
Drew
The price is CA $190
CA $212 total
includes taxes & fees
Oct 5 - Oct 6
Hotel On North
A house with a brick exterior, a green roof, and a driveway leading to a garage.

18. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (295 reviews)
"A cute, quiet getaway close to the Berkshire mountains!"
United States
Maya H.
The price is CA $191
CA $294 total
includes taxes & fees
Sep 30 - Oct 1
Berkshire Village Carriage House - Super Private!!
A two-story building with a central entrance, a covered porch, and a small balcony.

19. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (415 reviews)
"Large, clean, comfortable suite."
United States
Rena
The price is CA $140
CA $156 total
includes taxes & fees
Sep 30 - Oct 1
The Central Downtown Inn & Suites
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

20. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,159 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
The price is CA $111
CA $156 total
includes taxes & fees
Oct 1 - Oct 2
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.
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Top Cheshire Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"The problem with the suites is that the cooking smell of the adjoining kitchen can really permeate throughout the entire space. So whoever cooked like a tomato sauce or something before I was there, I could really smell it in the bedroom. The bed was very comfortable though. The room was clean. The bathroom could use some updating. The staff were very nice."
Bridget 1-night trip
Posted 2 hours ago
Berkshire Mountain Lodge

Find out more about Cheshire

Cheshire Castles information

Number of reviews
10,277
Accommodation
0 Castles
Lowest Price
CA $98
Highest Price
CA $379

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