Find Hotels with a Pool in Chatham, NY

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Chatham Hotels with a Pool

Tonight
Feb 21 - Feb 22
Tomorrow
Feb 22 - Feb 23
Next weekend
Feb 27 - Mar 1
In two weeks
Mar 6 - Mar 8

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, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
$139 nightly
The price is $155
Mar 1 - Mar 2
Total with taxes and fees
Element Lenox Berkshires
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, (736 reviews)
"Great property, very accommodating. "
United States
Shanice
$103 nightly
The price is $115
Feb 25 - Feb 26
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (1,009 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
$93 nightly
The price is $103
Mar 1 - Mar 2
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, (834 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
$67 nightly
The price is $75
Feb 23 - Feb 24
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, (850 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
$121 nightly
The price is $136
Mar 23 - Mar 24
Total with taxes and fees
Berkshire Mountain Lodge
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
$96 nightly
The price is $107
Feb 23 - Feb 24
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
$103 nightly
The price is $115
Feb 24 - Feb 25
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Outdoor spa tub

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,250 reviews)
"Excellent location and terrific space and amenities."
United States
Michelle
$126 nightly
The price is $141
Feb 22 - Feb 23
Total with taxes and fees
Vacation Village in the Berkshires
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (844 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
$84 nightly
The price is $94
Feb 23 - Feb 24
Total with taxes and fees
Berkshire Inn
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"The room and amenities were amazing. "
United States
Kathleen
$119 nightly
The price is $133
Mar 1 - Mar 2
Total with taxes and fees
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.
View all properties

Choose what matters most at hotels with a pool in Chatham

Breakfast included
Hot tub

The Annual Vacation Sale

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

Top Chatham Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great location, amenities, pool and hot tub for the kids, friendly staff, comfortable room."
Jennifer 2-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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: Hotel located near MVP Arena. Provides full, an indoor pool, and free self parking. Comfort Inn Glenmont - Albany South: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Offers a seasonal outdoor pool, an indoor pool, and buffet. The Yankee, Trademark Collection by Wyndham: 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.

Explore a world of travel with Expedia