Find Hotels with a Pool in Chatham, NY

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Check availability on Chatham Hotels with a Pool

Tonight
Jul 31 - Aug 1
Tomorrow
Aug 1 - Aug 2
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top Chatham Hotels with a Pool

The Old Inn On The Green
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished

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 NT$8,612
NT$10,392 total
includes taxes & fees
Aug 3 - Aug 4
The Old Inn On The Green
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (397)
"No frills but it was a great stay!"
The price is NT$3,269
NT$3,651 total
includes taxes & fees
Aug 18 - Aug 19
Sunset Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers

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

3.5 star property
9.0 out of 10, Wonderful, (682)
"Had a great time"
The price is NT$3,909
NT$4,781 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 NT$5,276
NT$5,893 total
includes taxes & fees
Aug 11 - Aug 12
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Indoor pool

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 NT$6,117
NT$6,833 total
includes taxes & fees
Aug 17 - Aug 18
Hilton Garden Inn Lenox Pittsfield
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (771)
"Was great loved the jacuzzi tub "
The price is NT$2,940
NT$3,284 total
includes taxes & fees
Aug 6 - Aug 7
Howard Johnson by Wyndham Lenox
Berkshire Mountain Lodge
Indoor pool, sun loungers

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (535)
"Excellent stay!"
The price is NT$3,113
NT$4,141 total
includes taxes & fees
Aug 17 - Aug 18
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

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 NT$5,035
NT$5,624 total
includes taxes & fees
Aug 25 - Aug 26
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Loved our visit"
Barbara 1-night trip
Posted 21 hours ago
The Red Lion 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.