A lake surrounded by autumn-colored trees and hills.

Search Resort Hotels in Cheshire from CA $97

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Check prices for these dates

Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4
In one month
Oct 16 - Oct 18
In two months
Nov 13 - Nov 15
No exact matches found, but these alternatives could be just right

Recommended hotels in Cheshire

Exterior

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (56 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $325
CA $343 total
includes taxes & fees
Sep 21 - Sep 22
Harbour House Inn
Courtyard

2. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (119 reviews)
"Loved the vibe!"
United States
Elizabeth
The price is CA $159
CA $174 total
includes taxes & fees
Sep 20 - Sep 21
The Springs Motel
Lobby

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,648 reviews)
"Great all around stay and lots for the kids to do"
United States
Sarah
The price is CA $132
CA $163 total
includes taxes & fees
Sep 21 - Sep 22
Vacation Village in the Berkshires
55-inch LCD TV with digital channels, printers

4. 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 CA $231
CA $258 total
includes taxes & fees
Sep 20 - Sep 21
The Revival House
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

5. 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, (1,003 reviews)
"Friendly staff. Good location."
United States
Joe
The price is CA $148
CA $165 total
includes taxes & fees
Oct 18 - Oct 19
Best Western Plus Berkshire Hills Inn & Suites
Desk, iron/ironing board, WiFi (free), bed sheets

6. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (905 reviews)
"great value"
United States
Horace
The price is CA $86
CA $97 total
includes taxes & fees
Sep 20 - Sep 21
FairBridge Inn Express
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

7. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"Was very recently renovated and done quite well."
United States
Robert
The price is CA $145
CA $162 total
includes taxes & fees
Sep 22 - Sep 23
The Yankee Inn
Standard Room, 1 King Bed, Non Smoking

8. Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (275 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 CA $101
CA $112 total
includes taxes & fees
Oct 15 - Oct 16
Rodeway Inn
Terrace/patio

9. 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, (156 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is CA $261
CA $292 total
includes taxes & fees
Sep 22 - Sep 23
The Trail in Adams - Berkshires’ Art Hotel
View from property

10. Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (345 reviews)
"Excellent service, excellent stay."
United States
Ahmet
The price is CA $138
CA $155 total
includes taxes & fees
Sep 22 - Sep 23
Williamstown Motel
Gazebo

11. Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (949 reviews)
"Loved this place"
United States
Jeremy
The price is CA $123
CA $144 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Corner Motel
Property entrance

12. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (916 reviews)
"Very nice and reasonably priced hotel for the region."
United States
Drew
The price is CA $197
CA $220 total
includes taxes & fees
Oct 18 - Oct 19
Hotel On North
Hypo-allergenic bedding available, desk, laptop workspace

13. 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, (1,000 reviews)
"Look good for being under constructikn"
United States
Debra
The price is CA $160
CA $179 total
includes taxes & fees
Oct 15 - Oct 16
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Terrace/patio

14. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (294 reviews)
"A cute, quiet getaway close to the Berkshire mountains!"
United States
Maya H.
The price is CA $188
CA $289 total
includes taxes & fees
Sep 20 - Sep 21
Berkshire Village Carriage House - Super Private!!
Property grounds

15. Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (1,000 reviews)
"The breakfast was amazing. All the fresh fruit you can imagine."
United States
Bill
The price is CA $118
CA $131 total
includes taxes & fees
Sep 20 - Sep 21
Willows Motel Williamstown
Family Bungalow

16. Huttopia Berkshires

Huttopia Berkshires
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (17 reviews)
"I lived that place, very peaceful, no noise, no shouting, and a very comfortable mattress, we had a great night's rest. And best of all, they accept dogs; my dog ​​was completely free to roam and happy."
United States
Dandara
The price is CA $135
CA $151 total
includes taxes & fees
Sep 20 - Sep 21
Huttopia Berkshires
Mountain view

17. Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (943 reviews)
"Great place"
United States
Donna
The price is CA $139
CA $155 total
includes taxes & fees
Sep 20 - Sep 21
Howard Johnson by Wyndham Williamstown
Property grounds

18. Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (639 reviews)
"Great spot with everything we needed"
United States
Christine
The price is CA $174
CA $194 total
includes taxes & fees
Sep 20 - Sep 21
Maple Terrace Motel
Hypo-allergenic bedding available, desk, laptop workspace

19. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,000 reviews)
"Clean room, great location. Perfect base for a weekend in the Berkshires."
United States
Alexandra
The price is CA $199
CA $223 total
includes taxes & fees
Oct 14 - Oct 15
Hotel Downstreet, an Ascend Collection Hotel
Desk, iron/ironing board, WiFi (free), bed sheets

20. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (925 reviews)
"Quiet location set back from road, comfortable beds and nice shower. Located right on Rt. 20 and near downtown."
United States
Ellen
The price is CA $119
CA $132 total
includes taxes & fees
Oct 18 - Oct 19
Berkshire Inn
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
"Liked everything! Mostly, the people. The staff was friendly and excited to serve us"
John 1-night trip
Posted 12 hours ago
Berkshires Untold

Find out more about Cheshire

Cheshire Resorts information

Number of reviews
11,753
Accommodation
12 Resorts
Lowest Price
CA $97
Highest Price
CA $343

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.
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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