Find Hotels with a Pool in Old Chatham, NY

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Check availability on Old Chatham Hotels with a Pool

Our top choices for Old Chatham hotels with a pool

Indoor pool
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
$131 nightly
The price is $146
Dec 16 - Dec 17
Total with taxes and fees
Element Lenox Berkshires
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
$108 nightly
The price is $121
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Meeting facility
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, (983)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$88 nightly
The price is $99
Dec 12 - Dec 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires 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, (1008)
"Great stay!"
United States
Ann
$89 nightly
The price is $100
Dec 17 - Dec 18
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
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, (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
$250 nightly
The price is $280
Dec 10 - Dec 11
Total with taxes and fees
Prospect Berkshires
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, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
$103 nightly
The price is $115
Dec 21 - Dec 22
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (784)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
$108 nightly
The price is $120
Jan 8 - Jan 9, 2026
Total with taxes and fees
Berkshire Mountain Lodge
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2168)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
$126 nightly
The price is $141
Dec 14 - Dec 15
Total with taxes and fees
Vacation Village in the Berkshires
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
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
$110 nightly
The price is $123
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Little Lion
Exterior
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
$79 nightly
The price is $88
Dec 10 - Dec 11
Total with taxes and fees
Howard Johnson by Wyndham 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 Old Chatham Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Staff is absolutely amazing "
Mitchell 2-night trip
Posted 2 days ago
Comfort Inn & Suites East Greenbush - Albany

Frequently asked questions

What are some hotels with pools in Old Chatham?
Chatham Travel Lodge: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires: Features free self parking, an indoor pool, and complimentary wireless internet access. Hyatt Place Albany/Downtown: Offers a health club, an indoor pool, and complimentary wired internet access. Hampton Inn & Suites Albany-Downtown: Offers 3 restaurants, an outdoor pool, and spa services. Albany Plaza Hotel: Hotel, 4-minute walk from MVP Arena. Features 2 restaurants, an indoor pool, and complimentary wireless internet access.
What is there to see and do in Old Chatham?
Make a point to visit attractions like Kinderhook Lake and Bousquet Ski Area. Discover sights such as Shaker Museum and Library during your stay.
When is the best time to book a hotel with a pool in Old Chatham?
Taking into account the local weather in Old Chatham is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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 Old Chatham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.

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