TOP Hotels with Pool in Cheshire, MA for 2026

Q: What are some accommodation options with pools in Cheshire?

Berkshire Mountain Lodge : Features free self parking, an indoor pool and complimentary wireless Internet access. Berkshires Untold : Provides a children's pool, an indoor pool and free self parking. Vacation Village in the Berkshires : Features daily, an indoor pool and free self parking. Hotel Downstreet, an Ascend Collection Hotel : Offers 3 restaurants, an outdoor pool and spa services. The Red Lion Inn : Features a seasonal outdoor pool, an indoor pool and buffet.

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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.

฿5,047 total

includes taxes & fees

17 Jun - 18 Jun

Berkshire Mountain Lodge

Pittsfield

Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.

฿5,578 total

includes taxes & fees

29 Jun - 30 Jun

Cozy Corner Motel

Williamstown

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

฿3,235 total

includes taxes & fees

8 Jun - 9 Jun

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Pittsfield

Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.

฿5,228 total

includes taxes & fees

22 Jun - 23 Jun

The Red Lion Inn

Stockbridge

Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.

฿7,628 total

includes taxes & fees

4 Jun - 5 Jun

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers

Maple Terrace Motel

Williamstown

Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.

฿4,175 total

includes taxes & fees

9 Jun - 10 Jun

Howard Johnson by Wyndham Lenox

Lenox

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

฿2,868 total

includes taxes & fees

1 Jun - 2 Jun

Willows Motel Williamstown

Williamstown

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

฿3,001 total

includes taxes & fees

30 Jun - 1 Jul

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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

10/10 Excellent

"We love the laid back shabby chic comfort of the Inn. It is our third visit in 2 years and a delightful getaway. The food is excellent. Breakfast has a good choice of menu options . We also love the pool"

Vacation Village in the Berkshires

4/10 Poor

"So after answering all questions that could only lead to a “decent” review here’s what happened. Check in was fine, it was a check in; friendly and we checked in. We get to the room and I leave to grab food for our dinner, my wife calls front desk because of awful noises upstairs, people stomping around like they’re getting paid to. I get back and she’s still on the phone after desk telling her everything is fixed… okayyy but we still hear incredible stomping. Lady insisted everything is fixed it must be a kid…..right but our room sounds like an industrial zone. Do we have to beg to be moved to a new room when this place is mostly vacant? Our food is cold and we’re on the phone again noise won’t stop even though I’m listening on ALL FLOORS for the source of noise, finally agrees to move us to a top floor in a new building. We haul our stuff over, keycards maintenance brought us don’t work. He says he’ll get new ones (very nice guy btw). ONE of the two new cards works after he comes back and he tries for a few minutes to get it to slide in at the perfect angle and velocity. Finally we get to settle into our new room for the last few hours we would be awake. Thanks for a wonderful finale to our one anniversary night away from kiddos. At least there was a tub to relax in this room. This place would have been fine if it weren’t for the horrible sound enhancing construction and front desk person who tried their best not to solve an easy problem."

The Porches Inn at Mass MoCA

8/10 Good

"Loved my room, staff were friendly and helpful, and the breakfast included delicious bagels and lox. I hope to return, though I will specifically ask to not stay in the building that houses reception. It’s an historic building so not soundproofed, and I could hear every guest checking in and out, and all the sounds from the kitchen during breakfast hours - it was just a little noisy for me."

Frequently asked questions

What are some accommodation options with pools in Cheshire?

Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. Berkshires Untold: Provides a children's pool, an indoor pool and free self parking. Vacation Village in the Berkshires: Features daily, an indoor pool and free self parking. Hotel Downstreet, an Ascend Collection Hotel: Offers 3 restaurants, an outdoor pool and spa services. The Red Lion Inn: Features a seasonal outdoor pool, an indoor pool and buffet.

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 Adams Theater 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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