A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

Next weekend
25 Sept - 27 Sept
In two weeks
2 Oct - 4 Oct
In one month
16 Oct - 18 Oct
In two months
13 Nov - 15 Nov
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 HK$1,990
HK$2,104 total
includes taxes & fees
21 Sept - 22 Sept
Harbour House Inn
Courtyard

2. The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (120 reviews)
"Loved the vibe!"
United States
Elizabeth
The price is HK$891
HK$978 total
includes taxes & fees
20 Sept - 21 Sept
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, (2,651 reviews)
"Great all around stay and lots for the kids to do"
United States
Sarah
The price is HK$746
HK$920 total
includes taxes & fees
21 Sept - 22 Sept
Vacation Village in the Berkshires
Desk, iron/ironing board, free WiFi, bed sheets

4. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (906 reviews)
"great value"
United States
Horace
The price is HK$487
HK$544 total
includes taxes & fees
1 Oct - 2 Oct
FairBridge Inn Express
Jetted bathtub

5. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Was very recently renovated and done quite well."
United States
Robert
The price is HK$910
HK$1,016 total
includes taxes & fees
22 Sept - 23 Sept
The Yankee Inn
55-inch LCD TV with digital channels, printers

6. 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 HK$1,299
HK$1,451 total
includes taxes & fees
20 Sept - 21 Sept
The Revival House
Minibar, iron/ironing board, free WiFi, bed sheets

7. 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 HK$567
HK$633 total
includes taxes & fees
14 Oct - 15 Oct
Rodeway Inn
Terrace/patio

8. 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 HK$1,471
HK$1,643 total
includes taxes & fees
22 Sept - 23 Sept
The Trail in Adams - Berkshires’ Art Hotel
Property grounds

9. 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 HK$663
HK$741 total
includes taxes & fees
20 Sept - 21 Sept
Willows Motel Williamstown
In-room safe, desk, laptop workspace, blackout curtains

10. 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 HK$830
HK$927 total
includes taxes & fees
18 Oct - 19 Oct
Best Western Plus Berkshire Hills Inn & Suites
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains

11. 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, (1,001 reviews)
"Look good for being under constructikn"
United States
Debra
The price is HK$910
HK$1,016 total
includes taxes & fees
21 Sept - 22 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
View from property

12. 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 HK$777
HK$868 total
includes taxes & fees
22 Sept - 23 Sept
Williamstown Motel
Gazebo

13. 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 HK$692
HK$813 total
includes taxes & fees
20 Sept - 21 Sept
Cozy Corner Motel
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains

14. 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 HK$1,123
HK$1,255 total
includes taxes & fees
14 Oct - 15 Oct
Hotel Downstreet, an Ascend Collection Hotel
Mountain view

15. 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 HK$784
HK$876 total
includes taxes & fees
20 Sept - 21 Sept
Howard Johnson by Wyndham Williamstown
Terrace/patio

16. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (295 reviews)
"A cute, quiet getaway close to the Berkshire mountains!"
United States
Maya H.
The price is HK$1,059
HK$1,647 total
includes taxes & fees
18 Sept - 19 Sept
Berkshire Village Carriage House - Super Private!!
Property entrance

17. 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 HK$1,106
HK$1,236 total
includes taxes & fees
18 Oct - 19 Oct
Hotel On North
Exterior

18. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (411 reviews)
"Large, clean, comfortable suite."
United States
Rena
The price is HK$769
HK$859 total
includes taxes & fees
8 Oct - 9 Oct
The Central Downtown Inn & Suites
Room

19. 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 HK$763
HK$852 total
includes taxes & fees
20 Sept - 21 Sept
Huttopia Berkshires
Desk, iron/ironing board, free WiFi, 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 HK$675
HK$754 total
includes taxes & fees
20 Sept - 21 Sept
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"Extremely friendly and helpful staff. Only complaint is very low toilet and slow internet speed."
robert 21-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Find out more about Cheshire

Cheshire Resorts information

Number of reviews
6,562
Accommodation
12 Resorts
Lowest Price
HK$544
Highest Price
HK$2,104

Frequently asked questions

What is Cheshire like for a resort holiday?
You deserve a holiday, and a resort is just the place to find all the amenities and services you need for a relaxing time in Cheshire. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for an amazing pool, shopping possibilities or activities for the youngsters.
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 directly by Jiminy Peak Mountain Resort. 6.5 mi (10.5 km) from Cheshire. Has ski-in/ski-out access, a fitness centre and a garden. COZY CABIN IN BERKSHIRES RESORT. - Ski resort directly by Jiminy Peak Mountain Resort. 6.6 mi (10.6 km) from Cheshire. Enjoy the ski-in/ski-out access, fitness centre and beach sunloungers.
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 temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm 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) away from the heart of the city. You can also search 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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