Find Hotels with a Pool in Chatham, NY

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Our top choices for Chatham hotels with a pool

Indoor pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (18 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
$139 nightly
The price is $155
Feb 22 - Feb 23
Total with taxes and fees
Element Lenox Berkshires
Indoor pool, seasonal outdoor pool, sun loungers

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
$93 nightly
The price is $103
Feb 22 - Feb 23
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (831 reviews)
"Staff was very friendly and helpful."
United States
Pamela
$69 nightly
The price is $77
Feb 16 - Feb 17
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (840 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
$121 nightly
The price is $136
Mar 15 - Mar 16
Total with taxes and fees
Berkshire Mountain Lodge
Indoor pool

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, (732 reviews)
"Great property, very accommodating. "
United States
Shanice
$107 nightly
The price is $120
Feb 22 - Feb 23
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (553 reviews)
"Great friendly staff"
United States
Pablo
$110 nightly
The price is $123
Feb 15 - Feb 16
Total with taxes and fees
The Little Lion
Indoor pool

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, (1,001 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
$102 nightly
The price is $114
Mar 7 - Mar 8
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (19 reviews)
"Excellent local stay - would recommend to all"
United States
Gentian
$196 nightly
The price is $219
Mar 11 - Mar 12
Total with taxes and fees
Prospect Berkshires
Indoor pool, sun loungers

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany
2.5 star property
Castleton-on-Hudson
8.6 out of 10, Excellent, (1,001 reviews)
"I have stayed here many times and have had good experiences always."
United States
Scott
$101 nightly
The price is $112
Feb 20 - Feb 21
Total with taxes and fees
Comfort Inn & Suites East Greenbush - Albany
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
$183 nightly
The price is $205
Mar 4 - Mar 5
Total with taxes and fees
The Red Lion 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.
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Choose what matters most at hotels with a pool in Chatham

Breakfast included
Hot tub

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Top Chatham Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Excellent location and terrific space and amenities."
Michelle 2-night trip
Posted 3 days ago
Vacation Village in the Berkshires

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. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Provides free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Features a seasonal outdoor pool, an indoor pool, and buffet. The Yankee, Trademark Collection by Wyndham: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Quality Inn Great Barrington: Provides 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.

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