Best Resorts in Cheshire

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Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15
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
$189 nightly
The price is $200
Jan 8 - Jan 9, 2026
Total with taxes and fees
Harbour House Inn
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, (1001)
"Very friendly and good Breakfast."
United States
Jesse
$76 nightly
The price is $85
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
$101 nightly
The price is $111
Dec 18 - Dec 19
Total with taxes and fees
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, (1004)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
$71 nightly
The price is $79
Dec 24 - Dec 25
Total with taxes and fees
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
$114 nightly
The price is $122
Dec 22 - Dec 23
Total with taxes and fees
Blooming Inn
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (13)
"New hotel very nice"
United States
joel
$131 nightly
The price is $146
Dec 22 - Dec 23
Total with taxes and fees
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, (988)
"Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . "
United States
Dwight
$94 nightly
The price is $105
Dec 19 - Dec 20
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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
$79 nightly
The price is $88
Dec 17 - Dec 18
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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)
"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
$100 nightly
The price is $112
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Gazebo
Cozy Corner Motel

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (887)
"Clean, Great Staff, Quiet"
United States
john
$79 nightly
The price is $88
Dec 17 - Dec 18
Total with taxes and fees
Cozy Corner Motel
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)
"We had a great visit! Easy to access, clean and comfortable. The studio had everything we needed!Great host!"
United States
Marina G.
$131 nightly
The price is $146
Jan 12 - Jan 13, 2026
Total with taxes and fees
In town, newly remodeled studio with private balcony
Terrace/patio
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
$161 nightly
The price is $170
Dec 17 - Dec 18
Total with taxes and fees
Blue Vista Motor Lodge
Reception
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
$69 nightly
The price is $77
Dec 17 - Dec 18
Total with taxes and fees
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
$108 nightly
The price is $119
Dec 17 - Dec 18
Total with taxes and fees
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
$77 nightly
The price is $87
Dec 21 - Dec 22
Total with taxes and fees
Berkshire Inn
Property grounds
Maple Terrace Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (589)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
$99 nightly
The price is $111
Dec 17 - Dec 18
Total with taxes and fees
Maple Terrace Motel
Check-in/check-out kiosk
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
$108 nightly
The price is $120
Jan 15 - Jan 16, 2026
Total with taxes and fees
Berkshire Mountain Lodge
Balcony
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
$85 nightly
The price is $95
Dec 17 - Dec 18
Total with taxes and fees
The Central Downtown Inn & Suites
Lobby lounge
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, (1002)
"Clean, pleasant staff and good breakfast. "
United States
Edward
$107 nightly
The price is $120
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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, (1004)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
$125 nightly
The price is $139
Jan 15 - Jan 16, 2026
Total with taxes and fees
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"A magical, magical New England weekend at The Red Lion Inn. The room was so warm, the bed and pillows were so comfortable and just the right firmness. The pool and hot tube were open, maybe bring a swimsuit if you are up for a soak in the hot tub on a cold snowy day or night. Check in was a breeze, staff were warm and welcoming. Highly recommend making reservations at their Tavern or Dining Area. Several small cafes and charming local shops close by for Christmas shopping"
Judith Pauline 1-night trip
Posted 12 hours ago
The Red Lion Inn

Find out more about Cheshire

Cheshire Resorts information

Number of reviews
12,013
Accommodation
33 Resorts
Lowest Price
$77
Highest Price
$200

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. Access to 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 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 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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