The Best Hotels with a Pool in Cheshire, MA from NT$2,791 in 2026

Q: What are some accommodations with pools in Cheshire?

Berkshire Mountain Lodge : Features free self parking, an indoor pool, and complimentary wireless internet access. 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. Berkshires Untold : Features a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn : Offers 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn : Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli.

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Cheshire Hotels with a Pool

Tonight

Tomorrow

Next weekend

In two weeks

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.

NT$3,703 total

includes taxes & fees

Jun 15 - Jun 16

Howard Johnson by Wyndham Lenox

Lenox

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

NT$2,791 total

includes taxes & fees

Jun 15 - Jun 16

Cozy Corner Motel

Williamstown

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

NT$3,149 total

includes taxes & fees

Jun 17 - Jun 18

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.

NT$4,947 total

includes taxes & fees

Jun 22 - Jun 23

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

Maple Terrace Motel

Williamstown

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

NT$4,063 total

includes taxes & fees

Jun 16 - Jun 17

Berkshire Mountain Lodge

Pittsfield

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

NT$5,004 total

includes taxes & fees

Jun 25 - Jun 26

The Springs Motel

New Ashford

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

NT$4,255 total

includes taxes & fees

Jun 15 - Jun 16

The Red Lion Inn

Stockbridge

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

NT$6,840 total

includes taxes & fees

Jun 22 - Jun 23

View all properties

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

"The inn is historic with a grand feel. The room was large and nicely furnished. The bed was very comfortable with plenty of pillows. Nice hot shower. Clean room. Food and service were great. The staff were professional and personable and made sure that you were happy with your stay. Would definitely return to this inn."

Hampton Inn & Suites Berkshires-Lenox

8/10 Good

"The staff were friendly and helpful. We especially appreciated the free delicious breakfast! The lady working in the breakfast area was meticulous about replacing food/drinks when supply was running low, and she frequently cleaned up the serving areas and the tables in the dining area. I never saw her stop! The only complaint I have is that the AC unit in our room was really loud."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"The view was great. It is in 10 to 30 minutes of places I wanted to visit. The staff went out of their way to accommodate me with the personal items I needed. I didn't need to use the Kayaks or pontoon that they rent to use on Lake Laural. The only drawback is no beach."

Frequently asked questions

What are some accommodations with pools in Cheshire?

Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. 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. Berkshires Untold: Features a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn: Offers 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli.

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 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.

Explore a world of travel with Expedia

Book Hotels with a Pool in Cheshire on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Cheshire Hotels with a Pool