A lake surrounded by autumn-colored trees and hills.

Cheshire Castle Hotels

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22
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
$254 nightly
The price is $268
Sep 29 - Sep 30
Total with taxes and fees
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
$114 nightly
The price is $125
Sep 30 - Oct 1
Total with taxes and fees
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
$122 nightly
The price is $136
Sep 29 - Sep 30
Total with taxes and fees
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
$69 nightly
The price is $77
Sep 29 - Sep 30
Total with taxes and fees
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
$77 nightly
The price is $85
Oct 4 - Oct 5
Total with taxes and fees
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
$108 nightly
The price is $121
Oct 27 - Oct 28
Total with taxes and fees
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
$166 nightly
The price is $185
Sep 29 - Sep 30
Total with taxes and fees
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
$135 nightly
The price is $151
Oct 14 - Oct 15
Total with taxes and fees
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
$106 nightly
The price is $118
Oct 18 - Oct 19
Total with taxes and fees
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
$93 nightly
The price is $104
Sep 29 - Sep 30
Total with taxes and fees
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
$111 nightly
The price is $124
Oct 29 - Oct 30
Total with taxes and fees
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
$93 nightly
The price is $104
Sep 29 - Sep 30
Total with taxes and fees
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
$175 nightly
The price is $195
Sep 29 - Sep 30
Total with taxes and fees
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
$98 nightly
The price is $110
Sep 29 - Sep 30
Total with taxes and fees
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
$79 nightly
The price is $88
Oct 29 - Oct 30
Total with taxes and fees
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
$109 nightly
The price is $122
Sep 29 - Sep 30
Total with taxes and fees
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
$152 nightly
The price is $170
Oct 5 - Oct 6
Total with taxes and fees
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.
$185 nightly
The price is $207
Sep 30 - Oct 1
Total with taxes and fees
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
$89 nightly
The price is $100
Oct 5 - Oct 6
Total with taxes and fees
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, (1,158 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
$109 nightly
The price is $121
Oct 1 - Oct 2
Total with taxes and fees
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"The temperature in the bedroom was very cold"
Malcolm 1-night trip
Posted less than an hour ago
Vacation Village in the Berkshires

Find out more about Cheshire

Cheshire Castles information

Number of reviews
9,118
Accommodation
0 Castles
Lowest Price
$77
Highest Price
$268

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