Book the Best Hotels with POOL in Chatham in 2026

Q: What are some accommodations 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

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Our top choices for Chatham 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.

CA $324 total

includes taxes & fees

Jun 13 - Jun 14

Berkshire Mountain Lodge

Pittsfield

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

CA $218 total

includes taxes & fees

Jun 14 - Jun 15

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.

CA $222 total

includes taxes & fees

Jun 22 - Jun 23

The Little Lion

Great Barrington

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

CA $152 total

includes taxes & fees

Jun 4 - Jun 5

The Red Lion Inn

Stockbridge

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

CA $305 total

includes taxes & fees

Jun 9 - Jun 10

Howard Johnson by Wyndham Lenox

Lenox

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

CA $122 total

includes taxes & fees

Jun 15 - Jun 16

Berkshire Travel Lodge

Austerlitz

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

CA $101 total

includes taxes & fees

May 31 - Jun 1

Berkshire Inn

Pittsfield

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

CA $125 total

includes taxes & fees

Jun 2 - Jun 3

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Choose what matters most at hotels with a pool in Chatham

Breakfast included

Hot tub

Top Chatham Hotel Reviews

The Red Lion Inn

10/10 Excellent

"We love the laid back shabby chic comfort of the Inn. It is our third visit in 2 years and a delightful getaway. The food is excellent. Breakfast has a good choice of menu options . We also love the pool"

Vacation Village in the Berkshires

4/10 Poor

"So after answering all questions that could only lead to a “decent” review here’s what happened. Check in was fine, it was a check in; friendly and we checked in. We get to the room and I leave to grab food for our dinner, my wife calls front desk because of awful noises upstairs, people stomping around like they’re getting paid to. I get back and she’s still on the phone after desk telling her everything is fixed… okayyy but we still hear incredible stomping. Lady insisted everything is fixed it must be a kid…..right but our room sounds like an industrial zone. Do we have to beg to be moved to a new room when this place is mostly vacant? Our food is cold and we’re on the phone again noise won’t stop even though I’m listening on ALL FLOORS for the source of noise, finally agrees to move us to a top floor in a new building. We haul our stuff over, keycards maintenance brought us don’t work. He says he’ll get new ones (very nice guy btw). ONE of the two new cards works after he comes back and he tries for a few minutes to get it to slide in at the perfect angle and velocity. Finally we get to settle into our new room for the last few hours we would be awake. Thanks for a wonderful finale to our one anniversary night away from kiddos. At least there was a tub to relax in this room. This place would have been fine if it weren’t for the horrible sound enhancing construction and front desk person who tried their best not to solve an easy problem."

Frequently asked questions

What are some accommodations 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 setting 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 into account the local weather in Chatham can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Chatham are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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