A lake surrounded by autumn-colored trees and hills.

Best Resorts in Cheshire

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Check prices for these dates

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27
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
9.6 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
$254 nightly
The price is $268
Nov 2 - Nov 3
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, (122 reviews)
"Loved the vibe!"
United States
Elizabeth
$88 nightly
The price is $96
Nov 1 - Nov 2
Total with taxes and fees
The Springs Motel
A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.

3. Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (283 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
$67 nightly
The price is $75
Nov 29 - Nov 30
Total with taxes and fees
Rodeway Inn
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, (928 reviews)
"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"
United States
Richard
$65 nightly
The price is $72
Nov 12 - Nov 13
Total with taxes and fees
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
$73 nightly
The price is $82
Nov 1 - Nov 2
Total with taxes and fees
Williamstown Motel
A living room with a fireplace, two sofas, and four black side tables.

6. The Revival House

The Revival House
3.0 star property
Adams
8.8 out of 10, Excellent, (43 reviews)
"Room 6 was much larger than expected! We arrived after hours and it was very easy to find our room."
United States
Katrina
$150 nightly
The price is $168
Nov 1 - Nov 2
Total with taxes and fees
The Revival House
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, (1,000 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
$89 nightly
The price is $99
Nov 1 - Nov 2
Total with taxes and fees
Willows Motel Williamstown
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

8. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,805 reviews)
"Great resort, great location very spacious."
United States
Marcos
$124 nightly
The price is $139
Nov 29 - Nov 30
Total with taxes and fees
Vacation Village in the Berkshires
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

9. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (930 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
$79 nightly
The price is $88
Oct 30 - Oct 31
Total with taxes and fees
Howard Johnson by Wyndham Lenox
An outdoor seating area with Adirondack chairs and potted plants.

10. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (964 reviews)
"Very clean and welcoming room. Staff man was very helpful and conscientious"
United States
Frank
$79 nightly
The price is $88
Nov 2 - Nov 3
Total with taxes and fees
Cozy Corner Motel
A kitchen with a countertop, a refrigerator, and a window.

11. The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (834 reviews)
"Outside my motel window, two wild bunnies grazed in the yard. This morning deer & fawns grazed in the field beside the parking lot. The bed was quite comfortable. Very nice stay."
United States
DONNA
$75 nightly
The price is $84
Nov 16 - Nov 17
Total with taxes and fees
The Villager Motel
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

12. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (940 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
$79 nightly
The price is $88
Nov 29 - Nov 30
Total with taxes and fees
Berkshire Inn
A modern living room with a dark archway, two white armchairs, a grey sofa, a round coffee table, and a floor lamp.

13. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.2 out of 10, Wonderful, (158 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
$151 nightly
The price is $169
Nov 8 - Nov 9
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
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)
"Great experience and Great onsite restaurant."
United States
mary ellen
$119 nightly
The price is $133
Nov 19 - Nov 20
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

15. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (967 reviews)
"Very nice hotel"
United States
Philip
$112 nightly
The price is $125
Nov 29 - Nov 30
Total with taxes and fees
Hotel On North
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

16. 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
$93 nightly
The price is $104
Nov 2 - Nov 3
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

17. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (431 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$99 nightly
The price is $111
Nov 1 - Nov 2
Total with taxes and fees
The Central Downtown Inn & Suites
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

18. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (301 reviews)
"Loved the easy Rail Trail access and peace and quite."
United States
Mary R.
$189 nightly
The price is $211
Oct 30 - Oct 31
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!
A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, and a small window.

19. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (957 reviews)
"Room was very clean. Tastefully decorated. Beds were comfortable. Would stay there next time we go to Williamstown,Mass."
United States
Barbara
$100 nightly
The price is $112
Nov 22 - Nov 23
Total with taxes and fees
Howard Johnson by Wyndham Williamstown
A garden with a swing set, a blue chair, and a flower bed.

20. Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (645 reviews)
"Perfect charming little hotel The couple at the front was very nice and helpful"
United States
yeraldine
$99 nightly
The price is $111
Nov 1 - Nov 2
Total with taxes and fees
Maple Terrace Motel
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

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Very charming, particularly the main house. We were at another structure off the main place which was perfectly nice but perhaps less charming."
Diane 1-night trip
Posted 13 hours ago
The Red Lion Inn

Find out more about Cheshire

Cheshire Resorts information

Number of reviews
8,050
Accommodation
8 Resorts
Lowest Price
$72
Highest Price
$268

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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