Hotels with Pool & Resorts in Old Chatham from AU$150

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Check availability on Old Chatham Hotels with Pool

Tonight
7 Dec - 8 Dec
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8 Dec - 9 Dec
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12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Best Old Chatham Hotels with 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
The price is AU$220
includes taxes & fees
14 Dec - 15 Dec
Element Lenox Berkshires
Indoor pool, seasonal outdoor pool, pool loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1005)
"Great stay!"
United States
Ann
The price is AU$150
includes taxes & fees
15 Dec - 16 Dec
The Yankee, Trademark Collection by Wyndham
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
The price is AU$154
includes taxes & fees
12 Dec - 13 Dec
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

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (704)
"We stay here every year and it never disappoints "
United States
Elizabeth
The price is AU$172
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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
The price is AU$166
includes taxes & fees
9 Dec - 10 Dec
Vacation Village in the Berkshires
2 indoor pools, 2 outdoor pools, pool umbrellas, pool loungers
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

3.5 star property
South Lee
9.0 out of 10, Wonderful, (797)
"Place was great!"
United States
Benjamin
The price is AU$255
includes taxes & fees
9 Dec - 10 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool, open 8:00 AM to 10:00 PM, pool 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
The price is AU$174
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn & Suites Berkshires-Lenox
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is AU$318
includes taxes & fees
8 Jan - 9 Jan 2026
The Red Lion Inn
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (781)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Iron/ironing board, free cots/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
The price is AU$185
includes taxes & fees
1 Jan - 2 Jan 2026
The Little Lion
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

Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

10/10 Excellent
"Yes"
Nelson 1-night trip
Posted 3 days ago
Hampton Inn & Suites Albany-Downtown

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 high-speed (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 such as 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 the local weather in Old Chatham into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Old Chatham are January, March, December and November, with each month seeing an average of 18 cm of snowfall.