Best Resorts in Cheshire

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Check prices for these dates

Next weekend
Apr 24 - Apr 26
In two weeks
May 1 - May 3
In one month
May 15 - May 17
In two months
Jun 12 - Jun 14
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
$227 nightly
The price is $240
May 4 - May 5
Total with taxes and fees
Harbour House Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (900 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
$73 nightly
The price is $82
Apr 26 - Apr 27
Total with taxes and fees
Berkshires Untold
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
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,000 reviews)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
$101 nightly
The price is $113
Apr 18 - Apr 19
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (899 reviews)
"We love Cozy Corner. It's a snug, safe, well-maintained, home away from home. Love the ample breakfast and the genuine welcome we receive every time."
United States
Ann
$84 nightly
The price is $93
Apr 28 - Apr 29
Total with taxes and fees
Cozy Corner Motel
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (447 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
$112 nightly
The price is $123
May 5 - May 6
Total with taxes and fees
Shaker Mill Inn
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
$138 nightly
The price is $148
Apr 19 - Apr 20
Total with taxes and fees
Blooming Inn
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 to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
United States
melissa
$150 nightly
The price is $168
Apr 19 - Apr 20
Total with taxes and fees
The Revival House
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (906 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
$108 nightly
The price is $120
May 17 - May 18
Total with taxes and fees
Berkshire Mountain Lodge
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,000 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
$101 nightly
The price is $113
May 3 - May 4
Total with taxes and fees
Quality Inn Lee - Lenox South
Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, free WiFi, bed sheets

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (240 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
$77 nightly
The price is $85
Apr 26 - Apr 27
Total with taxes and fees
Rodeway Inn
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
$151 nightly
The price is $169
Apr 26 - Apr 27
Total with taxes and fees
Element Lenox Berkshires
Desk, laptop workspace, blackout drapes, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
$69 nightly
The price is $76
Apr 21 - Apr 22
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Property grounds

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (600 reviews)
"Staff is very nice and the rooms are always clean!"
United States
Peter
$104 nightly
The price is $116
Apr 21 - Apr 22
Total with taxes and fees
Maple Terrace Motel
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, (121 reviews)
"set up great! very clean great location, WONDERFUL"
United States
laurie p.
$131 nightly
The price is $146
May 12 - May 13
Total with taxes and fees
In town, newly remodeled studio with private balcony
Reception

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (784 reviews)
"very clean, up to day, no thrills overnighter. perfect stop from NYC to VT skiing"
United States
Martin
$79 nightly
The price is $88
Apr 20 - Apr 21
Total with taxes and fees
The Villager Motel
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, (850 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
$78 nightly
The price is $87
May 7 - May 8
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Courtyard

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (95 reviews)
"Great quaint place. Great staff and very clean. "
United States
Janelle
$112 nightly
The price is $122
Apr 21 - Apr 22
Total with taxes and fees
The Springs Motel
Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
$380 nightly
The price is $424
Apr 19 - Apr 20
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Lake

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 spotless, staff was very kind!"
United States
Ilia
$99 nightly
The price is $111
Apr 26 - Apr 27
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean and cozy room, friendly staff, and fresh fruit for breakfast. Great location right next to Williams College."
United States
Phebe
$85 nightly
The price is $95
Apr 20 - Apr 21
Total with taxes and fees
Willows Motel Williamstown
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Cleanest and nicest room ever. Renovations ongoing but not disruptive. Excellent service."
Oleh 1-night trip
Posted 3 hours ago
Hampton Inn & Suites Berkshires-Lenox

Find out more about Cheshire

Cheshire Resorts information

Number of reviews
9,757
Accommodation
29 Resorts
Lowest Price
$76
Highest Price
$424

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 Susan B. Anthony Birthplace Museum 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.

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