The Best Hotels with a Pool in Cheshire, MA from NT$3,729 in 2026

Q: What are some accommodations with pools in Cheshire?

Vacation Village in the Berkshires : Aparthotel, 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 : Hotel, 6-minute walk from Massachusetts Museum of Contemporary Art. Offers daily, an indoor pool, and free self parking. The Yankee Inn : Provides a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge : Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold : Features 3 restaurants, an outdoor pool, and spa services.

A lake surrounded by autumn-colored trees and hills.

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Our top choices for Cheshire hotels with a pool

1. Hotel Downstreet, an Ascend Collection Hotel

North Adams

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

NT$5,826 total

includes taxes & fees

Aug 31 - Sep 1

2. The Yankee Inn

Lenox

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

NT$5,730 total

includes taxes & fees

Aug 2 - Aug 3

Indoor pool, outdoor pool, pool umbrellas

3. Vacation Village in the Berkshires

Williamstown

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

NT$3,729 total

includes taxes & fees

Aug 23 - Aug 24

4. The Springs Motel

New Ashford

Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.

NT$5,554 total

includes taxes & fees

Aug 2 - Aug 3

5. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

Swim indoors year-round at this welcoming retreat with an indoor pool, hot tub, and extended pool hours for ultimate relaxation.

NT$8,100 total

includes taxes & fees

Aug 27 - Aug 28

6. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.

NT$4,316 total

includes taxes & fees

Aug 31 - Sep 1

7. Berkshire Valley Inn

Williamstown

Splash into mountain adventure with seasonal poolside bliss and continental breakfast.

NT$5,989 total

includes taxes & fees

Aug 4 - Aug 5

8. Willows Motel Williamstown

Williamstown

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

NT$3,744 total

includes taxes & fees

Aug 4 - Aug 5

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Choose what matters most at hotels with a pool in Cheshire

Breakfast included

4 stars

Top Cheshire Hotel Reviews

The Red Lion Inn

8/10 Good

"Needs updating and cleaning.Pool ate in very bad shape"

Jiminy Peak Mountain Resort

10/10 Excellent

"Excellent "get away from it all" vibe on this little mountain resort. The drive and area is wooded and beautiful. The staff is AMAZING! Helpful, friendly, warm and welcoming. The rooms were cute and clean. Maybe a little dated and worn, but for the price they are perfect!! The pool was a bit small, but not crowded and deep. We also really enjoyed the walking trails, tennis court and pickle ball court. The adventure park was excellent for active kids. The ski lift ride was great and the alpine slide and mountain coaster is great for the whole family regardless of age!"

Frequently asked questions

What are some accommodations with pools in Cheshire?

Vacation Village in the Berkshires: Aparthotel, 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: Hotel, 6-minute walk from Massachusetts Museum of Contemporary Art. Offers daily, an indoor pool, and free self parking. The Yankee Inn: Provides a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold: Features 3 restaurants, an outdoor pool, and spa services.

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 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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Our top choices for Cheshire hotels with a pool