Find Hotels with a Pool in Chatham, NY from CA $110

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Check availability on Chatham Hotels with a Pool

Tonight
Aug 1 - Aug 2
Tomorrow
Aug 2 - Aug 3
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top Chatham Hotels with a Pool

The Old Inn On The Green
Relax in a serene bedroom with a large bed, window, and comfortable chair.

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (87)
"Beautiful room and property. Perfect weekend getaway!"
The price is CA $401
CA $484 total
includes taxes & fees
Aug 31 - Sep 1
The Old Inn On The Green
Deluxe Queen Room with 2 Queen Beds
Guest rooms lead to a covered walkway with a tiled floor.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (2)
"The chemical smell in the room was overwhelming. There was no personal contact We called the number provided and was told We would get a full refund."
The price is CA $137
CA $184 total
includes taxes & fees
Sep 1 - Sep 2
Deluxe Queen Room with 2 Queen Beds
Sunset Inn
Enjoy a refreshing swim in our pool surrounded by a tiled edge.

Sunset Inn

2.0 star property
7.6 out of 10, Good, (397)
"No frills but it was a great stay!"
The price is CA $148
CA $166 total
includes taxes & fees
Aug 18 - Aug 19
Sunset Inn
Devonfield Inn B&B
Enjoy a romantic meal for two on this serene patio, surrounded by lush greenery and a beautiful view.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
The price is CA $386
CA $431 total
includes taxes & fees
Sep 1 - Sep 2
Devonfield Inn B&B
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Swim laps in a serene, well-lit pool surrounded by a simple, functional design.

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (683)
"Had a great time"
The price is CA $172
CA $211 total
includes taxes & fees
Aug 6 - Aug 7
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (4)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is CA $223
CA $249 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Relax by the pool surrounded by lounge chairs and sunbeds, with views of the surrounding area and greenery.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is CA $241
CA $269 total
includes taxes & fees
Sep 1 - Sep 2
Hilton Garden Inn Lenox Pittsfield
Howard Johnson by Wyndham Lenox
Enjoy a refreshing swim in our pool surrounded by a serene landscape.

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (773)
"Was great loved the jacuzzi tub "
The price is CA $110
CA $122 total
includes taxes & fees
Sep 1 - Sep 2
Howard Johnson by Wyndham Lenox
Berkshire Mountain Lodge
Relax by the rectangular pool surrounded by lounge chairs and lush greenery.

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (535)
"Excellent stay!"
The price is CA $114
CA $158 total
includes taxes & fees
Sep 1 - Sep 2
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Enjoy a refreshing swim in our pool, surrounded by a spacious area with a clear view.

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Good lodgings in a great area to visit."
The price is CA $199
CA $223 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Berkshires-Lenox
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.

Top Chatham Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"Close to city center, safe and great costumer experience "
Mayra 1-night trip
Posted 1 day ago
Quality Inn

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. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Offers a health club, an indoor pool, and complimentary wired internet access. Best Western Plus Berkshire Hills Inn & Suites: Hotel located near MVP Arena. Features full, an indoor pool, and free self parking. Comfort Inn Glenmont - Albany South: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Offers buffet, an indoor pool, and free self parking.
What is there to see and do in Chatham?
The picturesque setting of Art Omi International Arts Center - Fields Sculpture Park and Kinderhook 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.