The Best Hotels with a Pool in Old Chatham, NY from ₩114,648 in 2026 | Expedia

Tracy Memorial Village Hall, Chatham, New York

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Check availability on Old Chatham Hotels with a Pool

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This weekend

Jun 12 - Jun 14

Next weekend

Jun 19 - Jun 21

Our top choices for Old 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.

₩193,536 total

includes taxes & fees

Jun 10 - Jun 11

Exterior

The Little Lion

Great Barrington

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

₩153,159 total

includes taxes & fees

Jun 10 - Jun 11

Outdoor pool, sun loungers

The Red Lion Inn

Stockbridge

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

₩335,558 total

includes taxes & fees

Jun 22 - Jun 23

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.

₩234,968 total

includes taxes & fees

Jun 14 - Jun 15

Exterior

Howard Johnson by Wyndham Lenox

Lenox

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

₩137,495 total

includes taxes & fees

Jun 9 - Jun 10

Indoor pool

Berkshire Mountain Lodge

Pittsfield

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

₩246,509 total

includes taxes & fees

Jun 10 - Jun 11

Outdoor pool

Berkshire Travel Lodge

Austerlitz

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

₩114,648 total

includes taxes & fees

Jun 9 - Jun 10

Seasonal outdoor pool

The Springs Motel

New Ashford

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

₩209,600 total

includes taxes & fees

Jun 9 - Jun 10

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Choose what matters most at hotels with a pool in Old Chatham

Breakfast included

4 stars

Top Old Chatham Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent

"I got the impression that Yankee Inn has quite a history, although it has been recently updated and renovated. The staff were available and friendly. At times I felt I was on a 1950s movie set, imagining Bing Crosby singing in my head. I ultimately extended my stay because it's location was a hub for the many surrounding activities--it's slightly over an hour drive to Hartford, and I was happy to leave the hustle and bustle of the city and return to the beauty of the Berkshires. I was surrounded by nature, but a grocery store, pharmacy, laundromat, and stores were also a short distance down the road. An extensive daily breakfast selection surpassed any I've recently had, and I've done my fair share of traveling."

Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

8/10 Good

"Property itself was fine. The room was fine. The only thing that I had a problem with was the fact that there was one elevator out of order which meant only one elevator was working, so checking in wasn’t terrible but when it was time to check out, we had to wait for the elevator for a very long time before before we can even even go down and basically had to miss breakfast because even even though we were gonna be down in time since it took so long for the elevator to get us and bring all of our stuff down, we missed all the food and so unfortunately, it seems like we missed out on the amenity of having a free breakfast and then we also missed out on having what we thought would be an easy checkout and leaving the hotel room and then proceeded to need to stand in the elevator hallway for about 15 to 20 minutes if not almost a half hour before there was enough room for us to get on an elevator and bring all of our stuff down that we had."

The Red Lion Inn

The Red Lion Inn

10/10 Excellent

"Ideal location if one is looking to stay in Stockbridge. The guest house we stayed in was quiet and comfortable. But our room was looking a little worn and in need of some updates, such as the carpet. The property has an excellent restaurant. The property was undergoing a renovation during our stay, so the parking situation was at first confusing, but we got the hang of it quickly,"

Frequently asked questions

What are some hotels with pools in Old Chatham?

Chatham Travel Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Hotel, 4-minute walk from MVP Arena. Provides 2 restaurants, an indoor pool, and complimentary wireless internet access. Hilton Albany: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. Hyatt Place Albany/Downtown: Provides a seasonal outdoor pool, an indoor pool, and buffet. Vacation Village in the Berkshires: Offers 3 restaurants, an outdoor pool, and spa services.

What is there to see and do in Old Chatham?

Make a point to visit attractions like Queechy Lake and Bousquet Ski Area. Discover sights such as Shaker Museum and Library during your stay.

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

Taking into account the local weather in Old Chatham 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 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Old Chatham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.

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