Search Hotel Resorts in Cheshire

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb
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)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
United States
alton
The price is ₹19,441
₹20,549 total
includes taxes & fees
7 Jan - 8 Jan 2026
Harbour House Inn
Lobby sitting area
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, (1001)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is ₹6,906
₹7,714 total
includes taxes & fees
6 Jan - 7 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
The price is ₹9,757
₹10,704 total
includes taxes & fees
18 Dec - 19 Dec
Shaker Mill Inn
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, (1003)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ₹7,148
₹7,984 total
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham
Front of property
Blooming Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (124)
"Excellent! Really fun space with beautiful objects all around you. One of a kind, well run, seamless experience. "
United States
Ben
The price is ₹5,920
₹11,044 total
includes taxes & fees
17 Dec - 18 Dec
Blooming Inn
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (12)
"New hotel very nice"
United States
joel
The price is ₹11,845
₹13,231 total
includes taxes & fees
22 Dec - 23 Dec
Element Lenox Berkshires
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, (987)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ₹8,382
₹9,363 total
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
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 ₹7,143
₹7,979 total
includes taxes & fees
16 Dec - 17 Dec
Howard Johnson by Wyndham Lenox
Exterior
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)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is ₹9,069
₹10,130 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Cozy Corner Motel

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (885)
"Clean, Great Staff, Quiet"
United States
john
The price is ₹6,754
₹7,973 total
includes taxes & fees
16 Dec - 17 Dec
Cozy Corner Motel
Single Room | In-room safe, desk, free WiFi, bed sheets
Blue Vista Motor Lodge

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (196)
"We did not use the hot tub the room was clean the only issue we had was with the heat but was resolved both times, views were spectacular especially the sun coming up! "
United States
Joyce
The price is ₹14,533
₹15,362 total
includes taxes & fees
16 Dec - 17 Dec
Blue Vista Motor Lodge
Exterior
The Villager Motel

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (764)
"It's very good for stay over"
United States
Frances
The price is ₹6,239
₹6,969 total
includes taxes & fees
17 Dec - 18 Dec
The Villager Motel
Courtyard
The Springs Motel

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (88)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is ₹10,325
₹11,327 total
includes taxes & fees
16 Dec - 17 Dec
The Springs Motel
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, (840)
"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 ₹7,621
₹8,512 total
includes taxes & fees
17 Dec - 18 Dec
Berkshire Inn
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (588)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is ₹8,952
₹9,999 total
includes taxes & fees
16 Dec - 17 Dec
Maple Terrace Motel
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (788)
"This place is so peaceful and the staff is always helpful "
United States
Leona
The price is ₹8,923
₹11,987 total
includes taxes & fees
8 Jan - 9 Jan 2026
Berkshire Mountain Lodge
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ₹8,075
₹9,020 total
includes taxes & fees
16 Dec - 17 Dec
The Central Downtown Inn & Suites
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1001)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is ₹9,765
₹10,908 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Berkshires-Lenox
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
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, (1004)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is ₹11,251
₹12,567 total
includes taxes & fees
8 Jan - 9 Jan 2026
Hotel Downstreet, an Ascend Collection Hotel
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 Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The room was fantastic, cozy as can be! Also, as soon as you walk into the lobby it looked wonderful! The Manager, Jennifer was so nice to talk too! She made sure everything with room, etc. was good! She was a delight!"
Mary 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about Cheshire

Cheshire Resorts information

Number of reviews
11,881
Accommodation
1 Resorts
Lowest Price
₹6,969
Highest Price
₹20,549

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?
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. Access to a sauna, a fitness centre and a 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 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 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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