A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov
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 AU$382
includes taxes & fees
29 Sept - 30 Sept
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 AU$177
includes taxes & fees
30 Sept - 1 Oct
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 AU$167
includes taxes & fees
30 Sept - 1 Oct
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 AU$99
includes taxes & fees
29 Sept - 30 Sept
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 AU$122
includes taxes & fees
4 Oct - 5 Oct
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 AU$172
includes taxes & fees
27 Oct - 28 Oct
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 AU$263
includes taxes & fees
29 Sept - 30 Sept
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 AU$215
includes taxes & fees
14 Oct - 15 Oct
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 AU$168
includes taxes & fees
18 Oct - 19 Oct
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 AU$148
includes taxes & fees
29 Sept - 30 Sept
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 AU$177
includes taxes & fees
29 Oct - 30 Oct
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 AU$148
includes taxes & fees
29 Sept - 30 Sept
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 AU$278
includes taxes & fees
29 Sept - 30 Sept
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 AU$159
includes taxes & fees
29 Sept - 30 Sept
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 AU$129
includes taxes & fees
29 Oct - 30 Oct
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 AU$165
includes taxes & fees
29 Sept - 30 Sept
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 AU$214
includes taxes & fees
5 Oct - 6 Oct
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 AU$301
includes taxes & fees
30 Sept - 1 Oct
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 AU$157
includes taxes & fees
30 Sept - 1 Oct
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
The price is AU$158
includes taxes & fees
1 Oct - 2 Oct
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Amazing!"
Gabriela 3-night trip
Posted 1 hour ago
Berkshires Untold

Find out more about Cheshire

Cheshire Castles information

Number of reviews
9,118
Accommodation
0 Castles
Lowest Price
AU$99
Highest Price
AU$382

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