TOP Hotels with Swimming Pool in Cheshire, MA for 2026

Q: What are some accommodation options 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. Berkshire Mountain Lodge : Provides free self parking, an indoor pool and complimentary wireless Internet access. The Yankee Inn : Features a seasonal outdoor pool, an indoor pool and buffet. Berkshires Untold : Features 3 restaurants, an outdoor pool and spa services.

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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.

₹18,381 total

includes taxes & fees

16 Aug - 17 Aug

Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

2. The Yankee Inn

Lenox

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

₹15,198 total

includes taxes & fees

2 Aug - 3 Aug

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.

₹12,710 total

includes taxes & fees

12 Aug - 13 Aug

4. The Springs Motel

New Ashford

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

₹16,225 total

includes taxes & fees

2 Aug - 3 Aug

5. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

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

₹12,718 total

includes taxes & fees

30 Aug - 31 Aug

6. 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.

₹24,359 total

includes taxes & fees

13 Aug - 14 Aug

7. Willows Motel Williamstown

Williamstown

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

₹11,066 total

includes taxes & fees

6 Aug - 7 Aug

8. The Porches Inn at Mass MoCA

North Adams

Float peacefully day or night at this 24-hour outdoor pool and hot tub sanctuary.

₹27,050 total

includes taxes & fees

17 Aug - 18 Aug

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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

"I gotta admit, I was nervous about staying at the Red Lion Inn. I knew it was popular, but I stayed in their "sister" place (the Little Lion) once because it was the only available hotel room in the area at short notice and that place is a DISASTER. However, now I understand why people who love the Red Lion Inn LOVE the Red Lion Inn. It's not pristine & shiny in a new hotel kinda way. But it's also the exact opposite of a bland, chain hotel with no character or interest. 250y of history pours out of every inch of this place, and in a good way. I didn't get a chance to take advantage of the gym, pool, or other amenities, though did eat in the courtyard one lunchtime and that was good. The staff are very attentive and appear to take real pride in working in such an iconic hotel. My only criticism is that I don't think the cleaning is quite up to scratch. Harder to clean 250yo hotel with rugs over ancient wood floors than a new construction with LVP, but findings long blonde hairs on my hotel room wasn't something I enjoyed (my entire family is either red or brunette). Would I stay there again? Yes. Room prices in the summer are insane, like most places in the Berkshires, but that's when I have to go to the Berkshires, so if they don't get my business in the future, it'll be because there are no rooms available or for some reason a different town is a better choice of location, not because I don't want to stay here. 1 word of warning: have dog? Call to make your reservation."

Vacation Village in the Berkshires

8/10 Good

"While not a top-notch place to stay, for the price it is a good value particularly given that you have more space for less cost than just a good motel room and can do some cooking and meal prep on your own. The check-in is always smooth and the accommodations reasonably comfortable. Setting is very nice, particularly if you get a room/suite that isn't looking onto the parking lot/driveway area. We continue to stay here, even though every stay finds something that wasn't caught in the room clean-up but not really a housekeepers problem - this time it was a failing toaster and a micro-wave that wanted to make a noise all the time."

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 accommodation options 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. Berkshire Mountain Lodge: Provides free self parking, an indoor pool and complimentary wireless Internet access. The Yankee Inn: Features a seasonal outdoor pool, an indoor pool and buffet. 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 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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Our top choices for Cheshire hotels with a pool