Search Hotels with Pool in Old Chatham

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Check availability on Old Chatham Hotels with Pool

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Old Chatham hotels with a pool

Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is ฿4,195
฿4,686 total
includes taxes & fees
4 Jan - 5 Jan 2026
Element Lenox Berkshires
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, (998)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ฿2,741
฿3,062 total
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool, seasonal outdoor pool, pool 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, (1000)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ฿2,879
฿3,216 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Yankee, Trademark Collection by Wyndham
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, pool loungers
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (16)
"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 ฿7,831
฿9,789 total
includes taxes & fees
26 Jan - 27 Jan 2026
Prospect Berkshires
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, (710)
"Great hospitality "
United States
regina maria
The price is ฿3,325
฿3,714 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"Old time charm and hot tub under the stars"
United States
Lori
The price is ฿4,630
฿6,561 total
includes taxes & fees
26 Jan - 27 Jan 2026
The Red Lion Inn
Indoor pool, open 8:00 AM to 10:00 PM, pool 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, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is ฿3,232
฿3,610 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Berkshires-Lenox
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, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is ฿3,974
฿4,438 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Lenox Pittsfield
Iron/ironing board, free cots/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, (548)
"Perfect for pets "
United States
Maria
The price is ฿3,418
฿3,818 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Little Lion
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (795)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is ฿3,066
฿4,119 total
includes taxes & fees
22 Jan - 23 Jan 2026
Berkshire Mountain Lodge
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

Top Old Chatham Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Yes"
Richard 3-night trip
Posted 7 days ago
The Red Lion Inn

Frequently asked questions

What are some hotels with pools in Old 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. Hyatt Place Albany/Downtown: Hotel located near MVP Arena. Provides full, an indoor pool and free self parking. Comfort Inn Glenmont - Albany South: Offers a seasonal outdoor pool, an indoor pool and buffet. Albany Plaza Hotel: Features a health club, an indoor pool and complimentary high-speed (wired) Internet access. The Yankee, Trademark Collection by Wyndham: Provides free self parking, 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.