Cheshire Hotels with Swimming Pool

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Check availability on Cheshire Hotels with Swimming Pools

Our top choices for Cheshire hotels with a pool

Indoor 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 RM563
RM629 total
includes taxes & fees
27 Jan - 28 Jan
Element Lenox Berkshires
Indoor pool

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, (1,000 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is RM397
RM444 total
includes taxes & fees
30 Jan - 31 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool, seasonal outdoor pool, pool loungers

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)
"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 RM375
RM419 total
includes taxes & fees
28 Jan - 29 Jan
The Yankee, Trademark Collection by Wyndham
Indoor pool

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (663 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is RM519
RM579 total
includes taxes & fees
23 Jan - 24 Jan
Hilton Garden Inn Lenox Pittsfield
2 indoor pools, 2 outdoor pools, pool umbrellas, pool 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, (824 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is RM456
RM588 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool, open 6:00 AM to 10 PM, pool 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, (1,000 reviews)
"Staff was pleasant and helpful, room spacey and all immaculate ."
United States
Barbara
The price is RM509
RM569 total
includes taxes & fees
10 Feb - 11 Feb
Hotel Downstreet, an Ascend Collection Hotel
Exterior

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 RM320
RM358 total
includes taxes & fees
22 Jan - 23 Jan
Howard Johnson by Wyndham Lenox
Indoor pool

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 RM400
RM537 total
includes taxes & fees
1 Feb - 2 Feb
Berkshire Mountain Lodge
Gazebo

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 RM281
RM332 total
includes taxes & fees
1 Feb - 2 Feb
Cozy Corner Motel
Seasonal outdoor pool

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 RM539
RM591 total
includes taxes & fees
26 Jan - 27 Jan
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.
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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
"The staff is super friendly and accommodating. The location is quiet. We stayed during the winter, but the lake view from the restaurant and breakfast area were really nice. The hotel was well kept and clean. We’ll definitely stay there again. "
Victor 2-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

What are some accommodation options 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 high-speed (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 the local weather in Cheshire into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.

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