Top 10 Hotels with Pool & Accommodation in Cheshire from NZ$147

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 buffet, an indoor pool and complimentary high-speed (wired) Internet access.

An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

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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.

includes taxes & fees

28 May - 29 May

Berkshire Mountain Lodge

Pittsfield

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

includes taxes & fees

26 May - 27 May

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Pittsfield

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

includes taxes & fees

28 May - 29 May

Willows Motel Williamstown

Williamstown

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

includes taxes & fees

26 May - 27 May

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.

includes taxes & fees

27 May - 28 May

Berkshire Inn

Pittsfield

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

includes taxes & fees

25 May - 26 May

Cozy Corner Motel

Williamstown

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

includes taxes & fees

31 May - 1 June

The Springs Motel

New Ashford

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

includes taxes & fees

25 May - 26 May

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Choose what matters most at hotels with a pool in Cheshire

Breakfast included

4 stars

Top Cheshire Hotel Reviews

Vacation Village in the Berkshires

8/10 Good

"The room was clean and spacious. The kitchen was equipped with all necessary supplies to cook a full meal. Great place to stay and relax or plan family fun!"

The Red Lion Inn

10/10 Excellent

"Every year my sisters and I go to the Red Lion to celebrate our mom’s birthday. It was one of her favorite places! We love the charm, the history and the “old fashioned” feel. Every guest room is different and they kindly upgraded me to a suite the last two times. The food at the restaurant is really good and we always love hearing the Jazz in the Lion’s Den on Sunday night. Can’t wait to return next year."

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"I was a bit distressed by the parking lot situation and with the garage and lot all dug up and torn apart it looked horrible. But the staff was super kind and helpful and the room was really nice and I liked everything else about it. I was a bit anxious when I pulled up. It would have been nice to know in advance. But our stay went great. (My dog and me). I would stay there again if I have another dog trial out in that area."

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 buffet, an indoor pool and complimentary high-speed (wired) Internet access.

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, Susan B. Anthony Birthplace Museum 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.

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