Search Resort Hotels in Cheshire from CA $115

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Check prices for these dates

Next weekend
May 29 - May 31
In two weeks
Jun 5 - Jun 7
In one month
Jun 19 - Jun 21
In two months
Jul 17 - Jul 19
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 CA $319
CA $337 total
includes taxes & fees
Jun 1 - Jun 2
Harbour House Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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, (1,002 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is CA $152
CA $170 total
includes taxes & fees
May 26 - May 27
Best Western Plus Berkshire Hills Inn & Suites
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (457 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is CA $139
CA $152 total
includes taxes & fees
May 25 - May 26
Shaker Mill Inn
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
The price is CA $166
CA $185 total
includes taxes & fees
Jun 1 - Jun 2
The Yankee Inn
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (136 reviews)
"The room was clean and comfortable. It was a quiet night's sleep as I believe I was the only one there. Breakfast was very plain and simple: English muffins and cinnamon toast, with no fruit or juice. Coffee was plentiful"
United States
Sarah
The price is CA $131
CA $214 total
includes taxes & fees
May 25 - May 26
Blooming Inn
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (946 reviews)
"Clean and great job staffing "
United States
Pedro
The price is CA $121
CA $166 total
includes taxes & fees
May 26 - May 27
Berkshire Mountain Lodge
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, (125 reviews)
"set up great! very clean great location, WONDERFUL"
United States
laurie p.
The price is CA $133
CA $218 total
includes taxes & fees
Jun 23 - Jun 24
In town, newly remodeled studio with private balcony
55-inch LCD TV with digital channels, printers

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is CA $215
CA $240 total
includes taxes & fees
May 25 - May 26
The Revival House
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)
"Great location "
United States
Edith
The price is CA $156
CA $174 total
includes taxes & fees
May 31 - Jun 1
Quality Inn Lee - Lenox South
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (907 reviews)
"Facilities were excellent. Staff was very helpful and very efficient & courteous in taking care of any concerns I had."
United States
Barbara J
The price is CA $112
CA $132 total
includes taxes & fees
May 31 - Jun 1
Cozy Corner Motel
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (958 reviews)
"Great stay!"
United States
Aditya
The price is CA $148
CA $166 total
includes taxes & fees
Jun 7 - Jun 8
Berkshires Untold
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is CA $181
CA $202 total
includes taxes & fees
May 27 - May 28
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Standard Room, 1 King Bed, Non Smoking

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (243 reviews)
"Found dead flies in the beds and the sheets were stained. I would not expect much from an inexpensive room but I do expect it to be clean."
United States
Heidi
The price is CA $111
CA $123 total
includes taxes & fees
May 25 - May 26
Rodeway Inn
BBQ/picnic area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very good, (2 reviews)
"After a little snafu with check-in (we had completed the form in advance and never received the room number text), we were able to get checked in with the virtual front desk. The inn was clean and well appointed and centrally located. The common areas felt inviting and useful for both the adults and kids. We would stay again."
United States
Samantha
The price is CA $153
CA $171 total
includes taxes & fees
Jun 9 - Jun 10
Hideaway Inn Lenox
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (856 reviews)
"Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax. "
United States
Jennifer
The price is CA $103
CA $115 total
includes taxes & fees
May 25 - May 26
Berkshire Inn
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (785 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is CA $109
CA $122 total
includes taxes & fees
May 27 - May 28
The Villager Motel
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (606 reviews)
"Very clean and comfortable room and grounds, pleasant and helpful hosts, relaxing setting. Highly recommended."
United States
David J.
The price is CA $151
CA $168 total
includes taxes & fees
May 26 - May 27
Maple Terrace Motel
Exterior

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
9.8 out of 10, Exceptional, (30 reviews)
"Cozy spot - everything was just right, exactly as described. Host was thoughtful and communicative and arrival/departure were very smooth. Would definitely stay here again! "
United States
Amy G.
The price is CA $93
CA $197 total
includes taxes & fees
May 25 - May 26
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Exterior

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (211 reviews)
"Great stay! "
United States
ALEKSey
The price is CA $253
CA $267 total
includes taxes & fees
May 27 - May 28
Blue Vista Motor Lodge
Courtyard

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (97 reviews)
"We enjoyed our stay. Staff was nice and the motel is set between several different towns to explore. We plan to stay again soon!"
United States
Shakeila
The price is CA $134
CA $147 total
includes taxes & fees
May 26 - May 27
The Springs 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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"The hotel was funky is a good way, I liked the design and layout of the room and the dining area."
Daniel 2-night trip
Posted 2 hours ago
Berkshires Untold

Find out more about Cheshire

Cheshire Resorts information

Number of reviews
8,416
Accommodation
29 Resorts
Lowest Price
CA $115
Highest Price
CA $337

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?
Here's our top-rated resort near Cheshire: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 20.6 mi (33.2 km) from Cheshire. Amenities include a sauna, a fitness center, and a terrace.
What can I do in Cheshire?
Mount Greylock State Reservation, St Mary's of the Assumption Church, and Susan B. Anthony Birthplace Museum are a few interesting places to visit nearby. In the area, other attractions include Mount Greylock and Wahconah Falls State Park.
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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