A lake surrounded by autumn-colored trees and hills.

Hotels with Pool & Resorts in Cheshire from NZ$133

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Check availability on Cheshire Hotels with Pool

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

Our top choices for Cheshire hotels with a pool

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is NZ$297
includes taxes & fees
12 July - 13 July
The Yankee Inn
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, (2,428 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is NZ$268
includes taxes & fees
22 July - 23 July
Vacation Village in the Berkshires
Outdoor pool

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (881 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is NZ$194
includes taxes & fees
19 July - 20 July
Howard Johnson by Wyndham Lenox
Exterior

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (924 reviews)
  • cleanliness
    Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
The price is NZ$183
includes taxes & fees
12 July - 13 July
Cozy Corner Motel
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, (1,003 reviews)
  • cleanliness
    Poolside bliss awaits with mountain views in this rejuvenating indoor pool and spa pool retreat.
The price is NZ$335
includes taxes & fees
22 July - 23 July
Hotel Downstreet, an Ascend Collection Hotel
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (127 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a spa pool to soothe tired muscles.
The price is NZ$299
includes taxes & fees
16 July - 17 July
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Indoor pool

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (689 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is NZ$413
includes taxes & fees
9 Aug - 10 Aug
Hilton Garden Inn Lenox Pittsfield
Outdoor pool

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.
The price is NZ$184
includes taxes & fees
12 July - 13 July
Willows Motel Williamstown
Meeting facility

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,009 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is NZ$417
includes taxes & fees
22 July - 23 July
The Red Lion Inn
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (486 reviews)
  • cleanliness
    Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
The price is NZ$133
includes taxes & fees
13 July - 14 July
Berkshire Travel 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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Choose what matters most at hotels with a pool in Cheshire

Breakfast included
4 stars

Top Cheshire Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Breakfast is great"
Beth 7-night trip
Posted 3 hours ago
Hampton Inn & Suites Berkshires-Lenox

Frequently asked questions

What are some accommodation options with pools in Cheshire?
The Yankee Inn: Features a seasonal outdoor pool, an indoor pool and buffet. Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge: Provides free self parking, an indoor pool and complimentary wireless Internet access. The Red Lion Inn: Features 3 restaurants, an outdoor pool and spa services. Berkshires Untold: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access.
What is there to see and do in Cheshire?
Surround yourself with nature at Mount Greylock State Reservation and Cheshire Reservoir. 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.