Search Resort Hotels in Cheshire from CA $91

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
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
9.8 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $298
CA $314 total
includes taxes & fees
Dec 1 - Dec 2
Harbour House Inn
A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

2. Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (285 reviews)
"The motel was clean and somewhat updated. Check in and check out was easy. Across the street was a yummy pizzeria."
United States
Joann
The price is CA $91
CA $102 total
includes taxes & fees
Dec 7 - Dec 8
Rodeway Inn
A patio area with outdoor furniture, a fire pit, and potted plants.

3. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (123 reviews)
"Loved the vibe!"
United States
Elizabeth
The price is CA $133
CA $146 total
includes taxes & fees
Nov 16 - Nov 17
The Springs Motel
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, (935 reviews)
"Friendly staff"
United States
William
The price is CA $100
CA $112 total
includes taxes & fees
Nov 9 - Nov 10
FairBridge Inn Express
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.

5. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (367 reviews)
"Very nice staff!"
United States
Marta
The price is CA $118
CA $132 total
includes taxes & fees
Nov 16 - Nov 17
Williamstown Motel
A building entrance with a large planter with purple flowers and a small tree.

6. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (981 reviews)
"Very nice hotel"
United States
Philip
The price is CA $164
CA $183 total
includes taxes & fees
Nov 29 - Nov 30
Hotel On North
A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

7. Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (1,002 reviews)
"Outstanding bed and breakfast in Williamstown, walking distance to the college, and also close to Mass MOCA. Will be staying there again. The fresh fruit was absolutely outstanding."
United States
Anuj
The price is CA $119
CA $133 total
includes taxes & fees
Nov 9 - Nov 10
Willows Motel Williamstown
A kitchen with a countertop, a refrigerator, and a window.

8. The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (839 reviews)
"Everything was so clean, staff at the front desk were kind, will definitely be back if we stay in the area again!"
United States
Khileigh
The price is CA $97
CA $109 total
includes taxes & fees
Dec 1 - Dec 2
The Villager Motel
A living room with a fireplace, two sofas, and four black side tables.

9. The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (44 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 $212
CA $237 total
includes taxes & fees
Nov 9 - Nov 10
The Revival House
A fenced outdoor area with a pool, lounge chairs, and umbrellas.

10. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (941 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
The price is CA $117
CA $131 total
includes taxes & fees
Nov 28 - Nov 29
Berkshire Inn
Indoor pool

11. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,837 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is CA $114
CA $142 total
includes taxes & fees
Nov 9 - Nov 10
Vacation Village in the Berkshires
A hotel room with a flat-screen TV, a wooden desk, a black office chair, a coffee maker, and a sign indicating a non-smoking room.

12. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (966 reviews)
"Very clean and welcoming room. Staff man was very helpful and conscientious"
United States
Frank
The price is CA $106
CA $125 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Corner Motel
A building with a covered parking area and a grassy front yard.

13. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (960 reviews)
"Room was very clean. Tastefully decorated. Beds were comfortable. Would stay there next time we go to Williamstown,Mass."
United States
Barbara
The price is CA $141
CA $158 total
includes taxes & fees
Nov 26 - Nov 27
Howard Johnson by Wyndham Williamstown
Room

14. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,004 reviews)
"Had a great time at this wonderful hotel."
United States
marwan
The price is CA $168
CA $188 total
includes taxes & fees
Nov 22 - Nov 23
Hotel Downstreet, an Ascend Collection Hotel
A garden with a swing set, a blue chair, and a flower bed.

15. Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (648 reviews)
"Perfect charming little hotel The couple at the front was very nice and helpful"
United States
yeraldine
The price is CA $140
CA $156 total
includes taxes & fees
Nov 9 - Nov 10
Maple Terrace Motel
A covered porch with white furniture and green chairs, surrounded by lush greenery.

16. 1896 House Country Inn & Motels

1896 House Country Inn & Motels
2.5 star property
Williamstown
6.8 out of 10, (459 reviews)
"Decent"
United States
Maryann
The price is CA $123
CA $137 total
includes taxes & fees
Nov 9 - Nov 10
1896 House Country Inn & Motels
An indoor swimming pool with clear water, tiled floors, and a blue wall.

17. 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, (258 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is CA $146
CA $163 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

18. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (435 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is CA $137
CA $153 total
includes taxes & fees
Nov 9 - Nov 10
The Central Downtown Inn & Suites
A wooden cabin with a porch and steps leading to a door, surrounded by snow.

19. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.4 out of 10, Very good, (1,004 reviews)
"Nice resort and friendly staff."
United States
Olga
The price is CA $175
CA $195 total
includes taxes & fees
Nov 17 - Nov 18
Jiminy Peak Mountain Resort
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

20. 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, (1,002 reviews)
"Room was spacious and clean"
United States
James
The price is CA $132
CA $148 total
includes taxes & fees
Dec 1 - Dec 2
Best Western Plus Berkshire Hills Inn & Suites
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.
View all properties

Learn more about Cheshire

Get away to romantic Cheshire! Enjoy the skiing, hiking, and natural setting.

See all hotels in Cheshire
A lake surrounded by autumn-colored trees and hills.

Top reviews in Cheshire

A building entrance with a large planter with purple flowers and a small tree.
Hotel On North

Hotel On North

Hotel On North
Pittsfield

10/10 Excellent

This is a great hotel. Large rooms, great amenities and a steak house restaurant that is superb. We like it so much we are staying an extra night.
Canada
alan
Reviewed October 8, 2026
Hotel On North

Frequently Asked Questions

What is Cheshire like for a resort vacation?

You deserve a vacation, and a resort is just the place to find all the amenities and services you need for a relaxing trip to Cheshire. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for a luxurious suite, shopping possibilities, or fun activities to try.

What's the best resort for my stay in Cheshire?

Our highest-rated resorts around Cheshire: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 6.5 mi (10.5 km) from Cheshire. Has ski-in/ski-out access, a fitness center, and a garden. COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 6.6 mi (10.6 km) from Cheshire. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 6.4 mi (10.4 km) from Cheshire. Access to ski-in/ski-out access, a fitness center, and an indoor pool.

What can I do in Cheshire?

Mount Greylock State Reservation and Cheshire Reservoir are a few of the interesting sights to visit. In the area, other attractions include St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center.

What's the weather like in Cheshire?

The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches 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) from the city center. Otherwise, look 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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