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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar
No exact matches found, but these alternatives could be just right

Recommended hotels in Cheshire

Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is HK$1,576
HK$1,666 total
includes taxes & fees
29 Jan - 30 Jan
Harbour House Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,001 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is HK$596
HK$665 total
includes taxes & fees
29 Jan - 30 Jan
Best Western Plus Berkshire Hills Inn & Suites
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is HK$1,084
HK$1,211 total
includes taxes & fees
29 Jan - 30 Jan
Element Lenox Berkshires
Miscellaneous

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,000 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is HK$762
HK$851 total
includes taxes & fees
4 Feb - 5 Feb
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (129 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is HK$758
HK$1,229 total
includes taxes & fees
29 Jan - 30 Jan
Blooming Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,002 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is HK$603
HK$673 total
includes taxes & fees
1 Feb - 2 Feb
Quality Inn Lee - Lenox South
Exterior

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Everything was great! "
Canada
Daphne
The price is HK$722
HK$807 total
includes taxes & fees
29 Jan - 30 Jan
The Yankee, Trademark Collection by Wyndham
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (829 reviews)
"Staff was very friendly and helpful."
United States
Pamela
The price is HK$616
HK$688 total
includes taxes & fees
18 Jan - 19 Jan
Howard Johnson by Wyndham Lenox
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (441 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is HK$847
HK$930 total
includes taxes & fees
26 Jan - 27 Jan
Shaker Mill Inn
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1,000 reviews)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is HK$765
HK$854 total
includes taxes & fees
23 Jan - 24 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (890 reviews)
"Excellent service and a beautifully decorated property."
United States
Ivana
The price is HK$540
HK$639 total
includes taxes & fees
1 Feb - 2 Feb
Cozy Corner Motel
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,000 reviews)
"Wonderful. Great hosts. Would 100% stay again"
United States
Ben
The price is HK$597
HK$666 total
includes taxes & fees
16 Jan - 17 Jan
Willows Motel Williamstown
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains

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)
"Staff was pleasant and helpful, room spacey and all immaculate ."
United States
Barbara
The price is HK$975
HK$1,090 total
includes taxes & fees
2 Feb - 3 Feb
Hotel Downstreet, an Ascend Collection Hotel
Exterior

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (197 reviews)
"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
United States
Jean
The price is HK$1,393
HK$1,472 total
includes taxes & fees
19 Jan - 20 Jan
Blue Vista Motor Lodge
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (769 reviews)
"clean modern and spacious room. comfortable king bed. "
United States
William
The price is HK$585
HK$653 total
includes taxes & fees
19 Jan - 20 Jan
The Villager Motel
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (595 reviews)
"Cute place"
United States
Lisa
The price is HK$772
HK$862 total
includes taxes & fees
19 Jan - 20 Jan
Maple Terrace Motel
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (818 reviews)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is HK$877
HK$1,132 total
includes taxes & fees
29 Jan - 30 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Mountain view

Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown
2.0 star property
Williamstown
6.6 out of 10, (899 reviews)
"Great affordable place to stay while in the northern Berkshires."
United States
PAUL
The price is HK$702
HK$784 total
includes taxes & fees
29 Jan - 30 Jan
Howard Johnson by Wyndham Williamstown
Property grounds

In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony
Shelburne Falls
10.0 out of 10, Exceptional, (119 reviews)
"set up great! very clean great location, WONDERFUL"
United States
laurie p.
The price is HK$741
HK$1,219 total
includes taxes & fees
10 Feb - 11 Feb
In town, newly remodeled studio with private balcony
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is HK$702
HK$784 total
includes taxes & fees
29 Jan - 30 Jan
Sunset 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

The Williams Inn

The Williams Inn

10/10 Excellent
"Accommodating staff!"
Kelly 1-night trip
Posted 23 hours ago
The Williams Inn

Find out more about Cheshire

Cheshire Resorts information

Number of reviews
13,119
Accommodation
33 Resorts
Lowest Price
HK$639
Highest Price
HK$1,666

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. Bentley Brook the perfect home base for exploring nearby Berkshire County - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 6.4 mi (10.4 km) from Cheshire. Enjoy the ski-in/ski-out access, sauna and fitness centre. Bentley Brook the perfect home base for exploring nearby Berkshire County - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 6.4 mi (10.4 km) from Cheshire. Amenities include ski-in/ski-out access, a sauna and a fitness centre. COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY. - Ski resort steps from Jiminy Peak Mountain Resort. 6.6 mi (10.6 km) from Cheshire. Access to ski-in/ski-out access, a fitness centre and beach sunloungers.
What can I do in Cheshire?
Mount Greylock State Reservation, St Mary's of the Assumption Church and Mount Greylock State Reservation Visitor Center are a few interesting places to visit nearby. In the area, other attractions include Mount Greylock and Brodie Mountain.
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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