Find Hotels with a Pool in Cheshire, MA

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Check availability on Cheshire Hotels with a Pool

Tonight
Dec 5 - Dec 6
Tomorrow
Dec 6 - Dec 7
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Top Cheshire Hotels with a Pool

Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is NT$4,101
NT$4,581 total
includes taxes & fees
Dec 11 - Dec 12
Element Lenox Berkshires
Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
The price is NT$2,794
NT$3,122 total
includes taxes & fees
Dec 11 - Dec 12
The Yankee, Trademark Collection by Wyndham
Meeting facility
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, (979)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is NT$2,875
NT$3,211 total
includes taxes & fees
Dec 12 - Dec 13
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool
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, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is NT$2,855
NT$3,189 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool, open 6:00 AM to 10 PM, sun loungers
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
North Adams
8.8 out of 10, Excellent, (1001)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is NT$3,354
NT$3,746 total
includes taxes & fees
Dec 20 - Dec 21
Hotel Downstreet, an Ascend Collection Hotel
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2163)
"We booked 2 rooms. Staff was friendly, rooms clean. "
United States
Jutta
The price is NT$2,788
NT$3,457 total
includes taxes & fees
Dec 7 - Dec 8
Vacation Village in the Berkshires
2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers
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

3.5 star property
South Lee
9.0 out of 10, Wonderful, (794)
"Place was great!"
United States
Benjamin
The price is NT$3,335
NT$4,274 total
includes taxes & fees
Dec 8 - Dec 9
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is NT$3,231
NT$3,609 total
includes taxes & fees
Dec 14 - Dec 15
Hampton Inn & Suites Berkshires-Lenox
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is NT$4,040
NT$5,912 total
includes taxes & fees
Jan 4 - 2026/1/5
The Red Lion Inn
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (777)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"All of the above "
Lois 1-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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Frequently asked questions

What are some accommodations with pools in Cheshire?
Harbour House Inn: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires: Provides free self parking, an indoor pool, and complimentary wireless internet access. Hotel Downstreet, an Ascend Collection Hotel: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Offers a health club, an indoor pool, and complimentary wired internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Provides 3 restaurants, an outdoor pool, and spa services.
What is there to see and do in Cheshire?
Take in the natural beauty with a stop at Mount Greylock State Reservation. Discover sights such as St Mary's of the Assumption Church, Mount Greylock State Reservation Visitor Center, and Mount Greylock during your stay.
When is the best time to book a hotel with a pool in Cheshire?
Taking into account the local weather in Cheshire is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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.