TOP Hotels with Swimming Pool in Chatham, NY for 2026

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

Comfort Inn Glenmont - Albany South : Features full, an indoor pool and free self parking. Berkshire Mountain Lodge : Offers free self parking, an indoor pool and complimentary wireless Internet access. Country Inn & Suites by Radisson, Downtown Albany New York : Offers a children's pool, an indoor pool and free self parking. Berkshires Untold : Offers 3 restaurants, an outdoor pool and spa services. Vacation Village in the Berkshires : Provides buffet, an indoor pool and free self parking.

Tracy Memorial Village Hall, Chatham, New York

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 Chatham Hotels with Swimming Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Chatham 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.

Emma

₹14,785 total

includes taxes & fees

15 Jun - 16 Jun

Berkshire Mountain Lodge

Pittsfield

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

Danielle

₹12,685 total

includes taxes & fees

31 May - 1 Jun

Vacation Village in the Berkshires

Williamstown

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

Ellen

₹13,904 total

includes taxes & fees

31 May - 1 Jun

Howard Johnson by Wyndham Lenox

Lenox

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

Dan

₹8,403 total

includes taxes & fees

7 Jun - 8 Jun

Berkshire Inn

Pittsfield

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

Donald W

₹9,333 total

includes taxes & fees

3 Jun - 4 Jun

Sunset Inn

Lee

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

pilar

₹11,116 total

includes taxes & fees

8 Jun - 9 Jun

The Little Lion

Great Barrington

Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.

Lisa

₹10,154 total

includes taxes & fees

11 Jun - 12 Jun

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Pittsfield

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

Camille

₹14,429 total

includes taxes & fees

31 May - 1 Jun

View all properties

Choose what matters most at hotels with a pool in Chatham

Breakfast included

Hot tub

Top Chatham Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Clean room great check in process smooth easy going. Jacuzzi was great, very cleaned!"

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Great location close to everything. The staff was very helpful. The breakfast was perfect in every way. The room was also perfect… nice little kitchen… No dishes or silverware but I sink and refrigerator microwave , coffee pot so just enough. Really comfortable bed!"

Comfort Inn Glenmont - Albany South

10/10 Excellent

"Arrival and checking went flawless. Very little was lost in translation with front desk and staff. The young lady that was taking care of breakfast was very helpful and friendly. Breakfast was very good and had a variety of selections. Parking went flawless and I felt very safe on the property. Just 1 little thing. The side door was always kept open didn't need key to access side door. Other than that thr stay was definitely worth the price."

The Red Lion Inn

10/10 Excellent

"Every year my sisters and I go to the Red Lion to celebrate our mom’s birthday. It was one of her favorite places! We love the charm, the history and the “old fashioned” feel. Every guest room is different and they kindly upgraded me to a suite the last two times. The food at the restaurant is really good and we always love hearing the Jazz in the Lion’s Den on Sunday night. Can’t wait to return next year."

Frequently asked questions

What are some accommodation options with pools in Chatham?

Comfort Inn Glenmont - Albany South: Features full, an indoor pool and free self parking. Berkshire Mountain Lodge: Offers free self parking, an indoor pool and complimentary wireless Internet access. Country Inn & Suites by Radisson, Downtown Albany New York: Offers a children's pool, an indoor pool and free self parking. Berkshires Untold: Offers 3 restaurants, an outdoor pool and spa services. Vacation Village in the Berkshires: Provides buffet, an indoor pool and free self parking.

What is there to see and do in Chatham?

The picturesque settings of Kinderhook Lake and Queechy Lake showcase the area's natural beauty. Discover sights such as The Mac-Haydn Theatre during your stay.

When is the best time to book a hotel with a pool in Chatham?

Taking the local weather in Chatham into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chatham are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

Explore a world of travel with Expedia

More ways to book

Book Hotels with Swimming Pool in Chatham on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Chatham Hotels with Swimming Pool