Hotels with Swimming Pool, Cheshire Massachusetts

Q: What are some accommodations with pools in Cheshire?

The Yankee Inn : Features a seasonal outdoor pool, an indoor pool, and buffet. Vacation Village in the Berkshires : Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. 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 wired internet access.

A lake surrounded by autumn-colored trees and hills.

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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, sun loungers

The Yankee Inn

Lenox

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

P10,376 total

includes taxes & fees

Jul 13 - Jul 14

Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

Williamstown

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

P9,204 total

includes taxes & fees

Jul 20 - Jul 21

Howard Johnson by Wyndham Lenox

Lenox

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

P6,794 total

includes taxes & fees

Jul 12 - Jul 13

Cozy Corner Motel

Williamstown

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

P6,368 total

includes taxes & fees

Jul 12 - Jul 13

Indoor pool, open 6:00 AM to 10 PM, sun loungers

Hotel Downstreet, an Ascend Collection Hotel

North Adams

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

P11,673 total

includes taxes & fees

Jul 20 - Jul 21

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.

P10,438 total

includes taxes & fees

Jul 16 - Jul 17

Hilton Garden Inn Lenox Pittsfield

Pittsfield

Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.

P14,617 total

includes taxes & fees

Jul 12 - Jul 13

Willows Motel Williamstown

Williamstown

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

P6,454 total

includes taxes & fees

Jul 12 - Jul 13

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Choose what matters most at hotels with a pool in Cheshire

Breakfast included

4 stars

Top Cheshire Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Breakfast is great"

The Red Lion Inn

10/10 Excellent

"Had a lovely 2 night stay at the Red Lion Inn. The front desk staff were very welcoming. The location was convenient to many nice shops and restaurants, as well as sites like the Norman Rockwell museum and the Divine Mercies chapel and grounds. This hotel is a wonderful blend of historic and modern..and the breakfast is great!"

Jiminy Peak Mountain Resort

8/10 Good

"The room was fine, the carpet was old and a bit musty. The fridge was helpful to have, and we used the coffee maker, would have preferred a Keurig. The bed was comfortable and the air conditioner worked fine. The furniture was nice, we liked the two separate bathroom sinks. Over a pleasant stay."

Frequently asked questions

What are some accommodations with pools in Cheshire?

The Yankee Inn: Features a seasonal outdoor pool, an indoor pool, and buffet. Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. 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 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 Mount Greylock 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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