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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 building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

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 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, (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 $94
CA $105 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 $131
CA $144 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, (934 reviews)
"Friendly staff"
United States
William
The price is CA $99
CA $111 total
includes taxes & fees
Nov 12 - Nov 13
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, (366 reviews)
"Excellent service, excellent stay."
United States
Ahmet
The price is CA $116
CA $129 total
includes taxes & fees
Nov 11 - Nov 12
Williamstown Motel
A building with a covered parking area and a grassy front yard.

6. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (958 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 $156 total
includes taxes & fees
Nov 22 - Nov 23
Howard Johnson by Wyndham Williamstown
A building entrance with a large planter with purple flowers and a small tree.

7. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (978 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.

8. 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 $118
CA $132 total
includes taxes & fees
Nov 15 - Nov 16
Willows Motel Williamstown
A kitchen with a countertop, a refrigerator, and a window.

9. The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (838 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 $96
CA $108 total
includes taxes & fees
Dec 2 - Dec 3
The Villager Motel
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

10. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,829 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is CA $112
CA $141 total
includes taxes & fees
Nov 8 - Nov 9
Vacation Village in the Berkshires
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

11. 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 $113
CA $126 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Inn
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 $104
CA $123 total
includes taxes & fees
Nov 17 - Nov 18
Cozy Corner Motel
Room

13. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,000 reviews)
"Had a great time at this wonderful hotel."
United States
marwan
The price is CA $167
CA $186 total
includes taxes & fees
Nov 18 - Nov 19
Hotel Downstreet, an Ascend Collection Hotel
A covered porch with white furniture and green chairs, surrounded by lush greenery.

14. 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 8 - Nov 9
1896 House Country Inn & Motels
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 $138
CA $155 total
includes taxes & fees
Nov 11 - Nov 12
Maple Terrace Motel
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

16. 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 $138
CA $155 total
includes taxes & fees
Nov 12 - Nov 13
The Central Downtown Inn & Suites
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 $139
CA $155 total
includes taxes & fees
Dec 4 - Dec 5
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A living room with a fireplace, two sofas, and four black side tables.

18. 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 $193
CA $216 total
includes taxes & fees
Nov 16 - Nov 17
The Revival House
A resort with multiple buildings, a parking area, and a mountainous backdrop.

19. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.4 out of 10, Very good, (1,001 reviews)
"Nice resort and friendly staff."
United States
Olga
The price is CA $173
CA $193 total
includes taxes & fees
Nov 13 - Nov 14
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, (1,001 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.
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

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