Search Resort Hotels in Cheshire from CA $90

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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 $295
CA $312 total
includes taxes & fees
Dec 2 - Dec 3
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, (284 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 $101 total
includes taxes & fees
Dec 6 - Dec 7
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 $132
CA $145 total
includes taxes & fees
Dec 1 - Dec 2
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, (934 reviews)
"Friendly staff"
United States
William
The price is CA $100
CA $111 total
includes taxes & fees
Nov 9 - Nov 10
FairBridge Inn Express
A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

5. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (366 reviews)
"Excellent service, excellent stay."
United States
Ahmet
The price is CA $117
CA $131 total
includes taxes & fees
Nov 16 - Nov 17
Williamstown Motel
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

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 $163
CA $182 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, (1,001 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 $132 total
includes taxes & fees
Nov 8 - Nov 9
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 $108 total
includes taxes & fees
Dec 6 - Dec 7
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 $210
CA $235 total
includes taxes & fees
Nov 8 - Nov 9
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 $116
CA $130 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, (2,833 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is CA $113
CA $141 total
includes taxes & fees
Nov 11 - Nov 12
Vacation Village in the Berkshires
An outdoor seating area with Adirondack chairs and potted plants.

12. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (965 reviews)
"Very clean and welcoming room. Staff man was very helpful and conscientious"
United States
Frank
The price is CA $105
CA $124 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Corner Motel
A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, and a small window.

13. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (959 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 $140
CA $157 total
includes taxes & fees
Nov 23 - Nov 24
Howard Johnson by Wyndham Williamstown
A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

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, (1,002 reviews)
"Had a great time at this wonderful hotel."
United States
marwan
The price is CA $167
CA $187 total
includes taxes & fees
Nov 23 - Nov 24
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 $139
CA $155 total
includes taxes & fees
Nov 8 - Nov 9
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 $122
CA $136 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
9.2 out of 10, Wonderful, (257 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is CA $144
CA $161 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, (434 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is CA $139
CA $155 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, (1,002 reviews)
"Nice resort and friendly staff."
United States
Olga
The price is CA $173
CA $194 total
includes taxes & fees
Nov 14 - Nov 15
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 $131
CA $146 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.
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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 multi-story hotel with a classic facade, large windows, and a prominent entrance.
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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