Find Hotels with a Pool in Chatham, NY

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Check availability on Chatham Hotels with a Pool

Our top choices for Chatham hotels with a pool

Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is ₩193,580
₩216,229 total
includes taxes & fees
Dec 21 - Dec 22
Element Lenox Berkshires
Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ₩110,533
₩123,465 total
includes taxes & fees
Dec 24 - Dec 25
The Yankee, Trademark Collection by Wyndham
Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (986)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ₩136,984
₩153,011 total
includes taxes & fees
Dec 16 - Dec 17
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (707)
"Great hospitality "
United States
regina maria
The price is ₩158,115
₩176,615 total
includes taxes & fees
Dec 17 - Dec 18
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ₩372,383
₩465,470 total
includes taxes & fees
Dec 14 - Dec 15
Prospect Berkshires
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (788)
"This place is so peaceful and the staff is always helpful "
United States
Leona
The price is ₩145,828
₩195,902 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Berkshire Mountain Lodge
Indoor pool
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is ₩152,500
₩170,342 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Lenox Pittsfield
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (547)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is ₩162,548
₩181,566 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Little Lion
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is ₩116,739
₩130,393 total
includes taxes & fees
Dec 14 - Dec 15
Howard Johnson by Wyndham Lenox
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1001)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is ₩152,500
₩170,342 total
includes taxes & fees
Dec 14 - Dec 15
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.
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Top Chatham Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Your staff is very courteous and yes my room was spotless. "
FELICA 3-night trip
Posted 5 hours ago
Vacation Village in the Berkshires

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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. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Provides a health club, an indoor pool, and complimentary wired internet access. Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. The Yankee, Trademark Collection by Wyndham: Offers a seasonal outdoor pool, an indoor pool, and buffet.
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.