Find Hotels with a Pool in Cheshire, MA

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Check availability on Cheshire Hotels with a Pool

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, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is NT$4,386
NT$4,900 total
includes taxes & fees
Jan 26 - Jan 27
Element Lenox Berkshires

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, (1,006 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is NT$3,093
NT$3,454 total
includes taxes & fees
Jan 24 - Jan 25
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"The hotel is very nice and clean. From the moment we checked in to check out, we had an amazing time. "
United States
Gina
The price is NT$2,924
NT$3,266 total
includes taxes & fees
Jan 29 - Jan 30
The Yankee, Trademark Collection by Wyndham

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (662 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is NT$4,037
NT$4,509 total
includes taxes & fees
Jan 23 - Jan 24
Hilton Garden Inn Lenox Pittsfield

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, (824 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is NT$3,551
NT$4,584 total
includes taxes & fees
Jan 22 - Jan 23
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,000 reviews)
"Staff was pleasant and helpful, room spacey and all immaculate ."
United States
Barbara
The price is NT$3,963
NT$4,427 total
includes taxes & fees
Feb 10 - Feb 11
Hotel Downstreet, an Ascend Collection Hotel

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (829 reviews)
"Staff was very friendly and helpful."
United States
Pamela
The price is NT$2,493
NT$2,785 total
includes taxes & fees
Jan 26 - Jan 27
Howard Johnson by Wyndham Lenox

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (816 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is NT$3,114
NT$4,184 total
includes taxes & fees
Feb 1 - Feb 2
Berkshire Mountain Lodge

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (891 reviews)
"Excellent service and a beautifully decorated property."
United States
Ivana
The price is NT$2,187
NT$2,587 total
includes taxes & fees
Feb 1 - Feb 2
Cozy Corner Motel

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.2 out of 10, Wonderful, (90 reviews)
"Great vibe. Comfortable great staff"
United States
Bart
The price is NT$4,196
NT$4,604 total
includes taxes & fees
Jan 26 - Jan 27
The Springs Motel
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.

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. Hotel Downstreet, an Ascend Collection Hotel: Offers free self parking, an indoor pool, and complimentary wireless internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Provides a health club, an indoor pool, and complimentary wired internet access. The Yankee, Trademark Collection by Wyndham: Features a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access.
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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