Find Hotels with a Pool in Chatham, NY

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Chatham Hotels with a Pool

Our top choices for Chatham hotels with a pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (22 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is AED 511
AED 570 total
includes taxes & fees
16 Mar - 17 Mar
Element Lenox Berkshires

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,012 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is AED 340
AED 380 total
includes taxes & fees
16 Mar - 17 Mar
The Yankee, Trademark Collection by Wyndham

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (743 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is AED 393
AED 439 total
includes taxes & fees
15 Mar - 16 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (870 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is AED 391
AED 518 total
includes taxes & fees
1 Apr - 2 Apr
Berkshire Mountain Lodge

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (838 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is AED 253
AED 283 total
includes taxes & fees
10 Mar - 11 Mar
Howard Johnson by Wyndham Lenox

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (554 reviews)
"Great friendly staff"
United States
Pablo
The price is AED 404
AED 451 total
includes taxes & fees
10 Mar - 11 Mar
The Little Lion

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
"owners was nice, room was clean"
United States
tom
The price is AED 349
AED 390 total
includes taxes & fees
10 Mar - 11 Mar
Sunset Inn

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,294 reviews)
"Excellent location and terrific space and amenities."
United States
Michelle
The price is AED 382
AED 467 total
includes taxes & fees
10 Mar - 11 Mar
Vacation Village in the Berkshires

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,006 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is AED 466
AED 521 total
includes taxes & fees
31 Mar - 1 Apr
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (846 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is AED 303
AED 339 total
includes taxes & fees
1 Apr - 2 Apr
Berkshire Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Choose what matters most at hotels with a pool in Chatham

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.

Top Chatham Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Chatham?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Comfort Inn Glenmont - Albany South: Hotel located near MVP Arena. Offers full, an indoor pool, and free self parking. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Offers free self parking, an indoor pool, and complimentary wireless internet access. Country Inn & Suites by Radisson, Downtown Albany New York: Features a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge: Offers a health club, an indoor pool, and complimentary wired internet access.
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.