Best Resorts in Cheshire

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Recommended hotels in Cheshire

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
$233 nightly
The price is $246
May 4 - May 5
Total with taxes and fees
Harbour House Inn

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
$68 nightly
The price is $74
May 13 - May 14
Total with taxes and fees
Pleasant Valley Motel West Stockbridge

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, (1,001 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
$106 nightly
The price is $118
May 3 - May 4
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (920 reviews)
"Such a cool and affordable place to stay in the Berkshires. Great lobby/bar with a good restaurant."
United States
Kathy
$89 nightly
The price is $99
May 4 - May 5
Total with taxes and fees
Berkshires Untold

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
"Great location "
United States
Edith
$107 nightly
The price is $120
May 17 - May 18
Total with taxes and fees
Quality Inn Lee - Lenox South

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (448 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
$102 nightly
The price is $112
May 4 - May 5
Total with taxes and fees
Shaker Mill Inn

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (919 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
$113 nightly
The price is $126
Apr 30 - May 1
Total with taxes and fees
Berkshire Mountain Lodge

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
$103 nightly
The price is $115
May 3 - May 4
Total with taxes and fees
The Yankee Inn

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (902 reviews)
"Immaculate room, great staff, very complete breakfast, best coffee I've had in any motel. Highly recommend for anyone visiting the Williamstown area "
United States
James
$84 nightly
The price is $93
May 3 - May 4
Total with taxes and fees
Cozy Corner Motel

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
$103 nightly
The price is $113
Apr 30 - May 1
Total with taxes and fees
The Springs Motel

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
$138 nightly
The price is $154
Apr 30 - May 1
Total with taxes and fees
The Revival House

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (135 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
$155 nightly
The price is $167
May 5 - May 6
Total with taxes and fees
Blooming Inn

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (241 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
$71 nightly
The price is $79
May 6 - May 7
Total with taxes and fees
Rodeway Inn

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (91 reviews)
"Clean rooms, friendly staff, pool was very clean and so is the hot tub. Breakfast was okay. Overall our stay was excellent. Highly recommended."
United States
Camille
$127 nightly
The price is $142
May 4 - May 5
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
$189 nightly
The price is $200
Apr 30 - May 1
Total with taxes and fees
UU Rowe Camp and Conference Center

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
$178 nightly
The price is $199
May 6 - May 7
Total with taxes and fees
Element Lenox Berkshires

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)
"Beautiful place- beautiful views "
United States
Yanis
$114 nightly
The price is $128
May 6 - May 7
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel

In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony
Shelburne Falls
10.0 out of 10, Exceptional, (122 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

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (852 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
$78 nightly
The price is $87
May 27 - May 28
Total with taxes and fees
Howard Johnson by Wyndham Lenox

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.
$392 nightly
The price is $438
Apr 30 - May 1
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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

Find out more about Cheshire

Cheshire Resorts information

Number of reviews
9,366
Accommodation
29 Resorts
Lowest Price
$74
Highest Price
$438

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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