TOP Hotels with Pool in Cheshire, MA for 2026

Q: What are some accommodation options with pools in Cheshire?

Hotel Downstreet, an Ascend Collection Hotel : Features daily, an indoor pool and free self parking. The Yankee Inn : Offers a seasonal outdoor pool, an indoor pool and buffet. Vacation Village in the Berkshires : Condo, 14-minute walk from Jiminy Peak Mountain Resort. Provides a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge : Features free self parking, an indoor pool and complimentary wireless Internet access. The Red Lion Inn : Hotel, 15-minute walk from National Shrine of the Divine Mercy. Features 3 restaurants, an outdoor pool and spa services.

A lake surrounded by autumn-colored trees and hills.

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 Pool

Tonight

Tomorrow

This weekend

Next weekend

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.

Rp2.550.664 total

includes taxes & fees

6 Jul - 7 Jul

The Red Lion Inn

Stockbridge

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

Rp4.213.005 total

includes taxes & fees

9 Jul - 10 Jul

Cozy Corner Motel

Williamstown

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

Rp1.861.084 total

includes taxes & fees

12 Jul - 13 Jul

Berkshire Travel Lodge

Austerlitz

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

Rp1.353.590 total

includes taxes & fees

6 Jul - 7 Jul

Berkshire Inn

Pittsfield

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

Rp1.800.012 total

includes taxes & fees

13 Jul - 14 Jul

Howard Johnson by Wyndham Lenox

Lenox

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

Rp1.980.209 total

includes taxes & fees

5 Jul - 6 Jul

Willows Motel Williamstown

Williamstown

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

Rp1.881.130 total

includes taxes & fees

13 Jul - 14 Jul

Berkshire Mountain Lodge

Pittsfield

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

Rp3.080.619 total

includes taxes & fees

2 Aug - 3 Aug

View all properties

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

10/10 Excellent

"A lovely stay at the Black Swan hotel in Lee for my birthday. Room was nice and comfortable, sweet balcony area to watch the sunset over the lake. Close to many attractions, ie, Norman Rockwell museum, outlets, pretty town, Botanical gardens and more. Would definitely go back again. Thank you"