Cheshire Hotels with Pool, Massachusetts: Cheshire Hotel Guide

Q: 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.

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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

12 Jul - 13 Jul

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

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

includes taxes & fees

16 Jul - 17 Jul

Cozy Corner Motel

Williamstown

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

includes taxes & fees

26 Jul - 27 Jul

The Red Lion Inn

Stockbridge

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

includes taxes & fees

22 Jul - 23 Jul

Berkshire Travel Lodge

Austerlitz

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

includes taxes & fees

19 Jul - 20 Jul

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

13 Jul - 14 Jul

Sunset Inn

Lee

Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.

includes taxes & fees

23 Jul - 24 Jul

Howard Johnson by Wyndham Lenox

Lenox

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

includes taxes & fees

13 Jul - 14 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 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."

Jiminy Peak Mountain Resort

8/10 Good

"Nice spacious room and very comfortable. Pretty quiet since Summer is off season. Only downside was it was very hot when we visited - common areas were not adequately air conditioned. Also, main restaurant/brewery was closed. We did enjoy are stay and is a nice central location in the Bershires."

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good

"The staff was incredibly helpful and made our weekend very enjoyable. With that being said there were a couple of minor issues that we suspect will be addressed. There were not enough towels by the pool after being told they were there. The hotel doesn’t have its own restaurant but there is an attached one you are subjected to their hours of operation. There are multiple restaurants to eat within walking distance."

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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