Search Resorts in Cheshire

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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar
No exact matches found, but these alternatives could be just right

Recommended hotels in Cheshire

Exterior
Harbour House Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"Nice place for a weekend away."
United States
Gregory
The price is AED 790
AED 835 total
includes taxes & fees
8 Jan - 9 Jan
Harbour House Inn
Lobby lounge
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
The price is AED 511
AED 570 total
includes taxes & fees
19 Jan - 20 Jan
Element Lenox Berkshires
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

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, (1002)
"Very friendly and good Breakfast."
United States
Jesse
The price is AED 281
AED 313 total
includes taxes & fees
25 Jan - 26 Jan
Best Western Plus Berkshire Hills Inn & Suites
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (1000)
"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 AED 360
AED 402 total
includes taxes & fees
9 Jan - 10 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property
Blooming Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (126)
"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
United States
Allison
The price is AED 331
AED 549 total
includes taxes & fees
11 Jan - 12 Jan
Blooming Inn
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (440)
"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 AED 407
AED 447 total
includes taxes & fees
13 Jan - 14 Jan
Shaker Mill Inn
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1004)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is AED 302
AED 337 total
includes taxes & fees
1 Feb - 2 Feb
Quality Inn Lee - Lenox South
In-room safe, desk, laptop workspace, iron/ironing board
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is AED 290
AED 324 total
includes taxes & fees
9 Jan - 10 Jan
Howard Johnson by Wyndham Lenox
Reception
The Villager Motel

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (768)
"It's very good for stay over"
United States
Frances
The price is AED 253
AED 283 total
includes taxes & fees
11 Jan - 12 Jan
The Villager Motel
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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, (73)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is AED 450
AED 503 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is AED 403
AED 450 total
includes taxes & fees
26 Jan - 27 Jan
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1010)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is AED 372
AED 415 total
includes taxes & fees
14 Jan - 15 Jan
The Yankee, Trademark Collection by Wyndham
Gazebo
Cozy Corner Motel

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (889)
"Excellent service and a beautifully decorated property."
United States
Ivana
The price is AED 255
AED 301 total
includes taxes & fees
1 Feb - 2 Feb
Cozy Corner Motel
Courtyard
The Springs Motel

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (90)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is AED 466
AED 511 total
includes taxes & fees
8 Jan - 9 Jan
The Springs Motel
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1002)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is AED 426
AED 476 total
includes taxes & fees
2 Feb - 3 Feb
Hotel Downstreet, an Ascend Collection Hotel
Exterior
Blue Vista Motor Lodge

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (197)
"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 AED 656
AED 693 total
includes taxes & fees
12 Jan - 13 Jan
Blue Vista Motor Lodge
Lobby
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (807)
"great stall and friendly pet friendly place"
United States
bonnie
The price is AED 362
AED 487 total
includes taxes & fees
1 Feb - 2 Feb
Berkshire Mountain Lodge
Property grounds
In town, newly remodeled studio with private balcony

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)
"set up great! very clean great location, WONDERFUL"
United States
laurie p.
The price is AED 349
AED 574 total
includes taxes & fees
13 Jan - 14 Jan
In town, newly remodeled studio with private balcony
Property grounds
Willows Motel Williamstown

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (999)
"Convenient location & a clean room"
United States
Stephanie
The price is AED 281
AED 314 total
includes taxes & fees
8 Jan - 9 Jan
Willows Motel Williamstown
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (841)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is AED 291
AED 325 total
includes taxes & fees
29 Jan - 30 Jan
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

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

10/10 Excellent
"Very good "
Fernando 5-night trip
Posted 1 day ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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. Enjoy the sauna, fitness center, and terrace.
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 Adams Theater and Mount Greylock.
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.