Find Hotels with a Pool in Cheshire, MA

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Our top choices for Cheshire hotels with a pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (22 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is NT$4,404
NT$4,919 total
includes taxes & fees
Mar 26 - Mar 27
Element Lenox Berkshires

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is NT$2,935
NT$3,279 total
includes taxes & fees
Mar 15 - Mar 16
The Yankee, Trademark Collection by Wyndham

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (869 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is NT$3,369
NT$4,471 total
includes taxes & fees
Apr 1 - Apr 2
Berkshire Mountain Lodge

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (895 reviews)
"Excellent service and a beautifully decorated property."
United States
Ivana
The price is NT$2,481
NT$2,924 total
includes taxes & fees
Mar 15 - Mar 16
Cozy Corner Motel

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (836 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is NT$2,186
NT$2,442 total
includes taxes & fees
Mar 8 - Mar 9
Howard Johnson by Wyndham Lenox

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (596 reviews)
"Cute place"
United States
Lisa
The price is NT$3,136
NT$3,503 total
includes taxes & fees
Mar 15 - Mar 16
Maple Terrace Motel

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, (84 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is NT$4,182
NT$4,671 total
includes taxes & fees
Mar 22 - Mar 23
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (93 reviews)
"I’ve stayed here a few times. Super quaint and a reasonable distance to lots of great places. Very affordable."
United States
Jennifer
The price is NT$4,411
NT$4,838 total
includes taxes & fees
Mar 12 - Mar 13
The Springs Motel

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
"owners was nice, room was clean"
United States
tom
The price is NT$3,010
NT$3,362 total
includes taxes & fees
Mar 8 - Mar 9
Sunset Inn

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,005 reviews)
"Very clean and warm room, kind staff, many fresh fruits for breakfast. Wonderful stay in cold January."
United States
ALEXEI
The price is NT$2,424
NT$2,707 total
includes taxes & fees
Apr 1 - Apr 2
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.

Choose what matters most at hotels with a pool in Cheshire

Top Cheshire Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Cheshire?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. The Williams Inn: Features a seasonal outdoor pool, an indoor pool, and buffet. The Yankee, Trademark Collection by Wyndham: Offers a health club, an indoor pool, and complimentary wired internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli.
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.

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