🏊 Top 10 Cheshire Hotels with Swimming Pool | Expedia Malaysia

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

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

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Check availability on Cheshire Hotels with Swimming Pools

Tonight

23 Jun - 24 Jun

Tomorrow

24 Jun - 25 Jun

This weekend

26 Jun - 28 Jun

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.

RM664 total

includes taxes & fees

7 Jul - 8 Jul

Indoor pool

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.

RM792 total

includes taxes & fees

6 Jul - 7 Jul

Gazebo

Cozy Corner Motel

Williamstown

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

RM429 total

includes taxes & fees

12 Jul - 13 Jul

Exterior

The Red Lion Inn

Stockbridge

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

RM886 total

includes taxes & fees

1 Jul - 2 Jul

Outdoor pool

Berkshire Travel Lodge

Austerlitz

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

RM313 total

includes taxes & fees

29 Jun - 30 Jun

Seasonal outdoor pool

The Springs Motel

New Ashford

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

RM505 total

includes taxes & fees

24 Jun - 25 Jun

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.

RM596 total

includes taxes & fees

29 Jun - 30 Jun

Exterior

Howard Johnson by Wyndham Lenox

Lenox

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

RM457 total

includes taxes & fees

24 Jun - 25 Jun

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Choose what matters most at hotels with a pool in Cheshire

Breakfast included

4 stars

Top Cheshire Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent

"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."

The Red Lion Inn

The Red Lion Inn

8/10 Good

"I did not stay in the main building but had a room in a separate building on the same block. I quite liked my room away from the inn. It was roomy, quiet, across the street from a church, easy walk to the cafe, and there was a bunny 🐰 eating grass outside each night. I think I will request such a room away from the hubbub when I return. The food at the Red Lion's Inn's 'Widow's' tavern was delicious. Just know the buildings are indeed OLD so if you are seeking great water pressure or modern vibe, this is not your place. Love the history of this place!"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Had a wonderful stay. Staff is friendly and helpful. Breakfast was great, especially the automatic pancake maker. Had a wonderful dinner from Mint restaurant. The room was very clean and had the most comfortable hotel bed ever. The shower was a gleaming white as if it had never been used. The swan soap dish was a lovely touch. The view of the lake and mountains is spectacular. Would definitely stay here again."

Frequently asked questions

What are some accommodation options with pools in Cheshire?

Hotel Downstreet, an Ascend Collection Hotel: Features daily, an indoor pool and free self parking. Berkshire Mountain Lodge: Offers 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. Provides a children's pool, an indoor pool and free self parking. The Yankee Inn: Features a seasonal outdoor pool, an indoor pool and buffet. Berkshires Untold: Hotel, 15-minute walk from National Shrine of the Divine Mercy. Offers 3 restaurants, an outdoor pool and spa services.

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 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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