TOP Hotels with Pool in Cheshire, MA for 2026 | Expedia.co.th

A lake surrounded by autumn-colored trees and hills.

A lake surrounded by autumn-colored trees and hills.

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Check availability on Cheshire Hotels with Pool

Tonight

15 Jul - 16 Jul

Tomorrow

16 Jul - 17 Jul

This weekend

17 Jul - 19 Jul

Next weekend

24 Jul - 26 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

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

฿7,069 total

includes taxes & fees

16 Jul - 17 Jul

Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

Williamstown

Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.

฿5,835 total

includes taxes & fees

19 Jul - 20 Jul

Gazebo

Cozy Corner Motel

Williamstown

Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.

฿3,575 total

includes taxes & fees

22 Jul - 23 Jul

Indoor pool, open 6:00 AM to 10 PM, pool loungers

Hotel Downstreet, an Ascend Collection Hotel

North Adams

Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.

฿6,433 total

includes taxes & fees

20 Jul - 21 Jul

Outdoor pool

Willows Motel Williamstown

Williamstown

Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.

฿3,518 total

includes taxes & fees

16 Jul - 17 Jul

Exterior

Howard Johnson by Wyndham Lenox

Lenox

Summertime splashes await at this refreshing outdoor pool oasis in Lenox.

฿3,703 total

includes taxes & fees

16 Jul - 17 Jul

Outdoor pool

Berkshire Travel Lodge

Austerlitz

Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.

฿2,531 total

includes taxes & fees

16 Jul - 17 Jul

Seasonal outdoor pool

Berkshire Inn

Pittsfield

Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.

฿3,366 total

includes taxes & fees

20 Jul - 21 Jul

View all properties

Choose what matters most at hotels with a pool in Cheshire

Breakfast included

4 stars

Top Cheshire Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent

"It's an attractive, well run hotel. I like the idea that breakfast is included. It is reasonably close to Tanglewood."

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Staff was fabulous and extremely helpful and friendly. Valey parking was terrific!!! and FREE Great to have since we had to park at the bank next to the hotel while there was construction in front of the building. Rooms were tidy and very clean Breakfast was excellent with a large variety of offerings"

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent

"Everything about our stay was wonderful We made a last-minute decision just to go up for a night and we were able to use several amenities like the chairlift ride for sightseeing. The pool a few times which was at a very comfortable temperature just to get in and relax We were able to use their locker room to take showers before we left to go home on our trip The room was very clean. The bed was comfortable plenty of pillows to choose from. Every staff member we encountered were very accommodating and friendly"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"I found the staff very helpful, especially the young man who worked over night. We experienced a slight problem, and he could not have been nicer. He represented the hotel extremely well. Breakfast was uninspiring but generally good. The view from the breakfast room is lovely. The common areas seem a little tired, but the room was very good value - especially as we overlooked the lake. The location is wonderful for Lee, Lenox, Stockbridge, all the cultural centers and the Mass Pike. A beach is adjacent for swimming. We plan to return next year."

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. The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool and buffet. 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 Susan B. Anthony Birthplace Museum 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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