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Find Hotels with a Pool in Chatham, NY

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Check availability on Chatham Hotels with a Pool

Tonight
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Chatham hotels with a pool

1. Berkshire Travel Lodge

Berkshire Travel Lodge
Austerlitz
  • Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
NT$2,151
NT$2,409 total
includes taxes & fees
Sep 1 - Sep 2
Berkshire Travel Lodge

2. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
NT$5,036
NT$5,625 total
includes taxes & fees
Sep 14 - Sep 15
The Yankee Inn

3. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
  • Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
NT$3,920
NT$4,379 total
includes taxes & fees
Sep 23 - Sep 24
Holiday Inn Express Hotel & Suites Great Barrington by IHG

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
NT$3,015
NT$4,080 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
NT$5,021
NT$7,192 total
includes taxes & fees
Sep 8 - Sep 9
The Red Lion Inn

6. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
NT$2,518
NT$2,813 total
includes taxes & fees
Aug 31 - Sep 1
Howard Johnson by Wyndham Lenox

7. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
NT$4,155
NT$4,641 total
includes taxes & fees
Sep 24 - Sep 25
Hampton Inn & Suites Berkshires-Lenox

8. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
NT$3,729
NT$4,789 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Club Vacations Oak 'n Spruce Resort

9. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
NT$3,586
NT$4,005 total
includes taxes & fees
Sep 2 - Sep 3
The Little Lion

10. Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany
Castleton-on-Hudson
  • Dive into refreshing bliss at this East Greenbush hotel's indoor pool, complete with cozy sun loungers for ultimate relaxation.
NT$3,844
NT$4,267 total
includes taxes & fees
Sep 8 - Sep 9
Comfort Inn & Suites East Greenbush - Albany
View all properties

Choose what matters most at hotels with a pool in Chatham

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chatham Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"This particular room, the mattress on the sifabed is worn and uncomfortable. Needs a real topper, or to be replaced. I slept on the couch, not in the bed, with a sheet on it."
marsha 4-night trip
Posted 9 hours ago
Vacation Village in the Berkshires
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

8/10 Good
"Room was very clean — much cleaner than the common areas. Breakfast was good. Nice gas station with convenience store next door."
Aaron 1-night trip
Posted 13 hours ago
Comfort Inn & Suites East Greenbush - Albany
The Yankee Inn

The Yankee Inn

8/10 Good
"Almost two hotels in one. Several structures. One nicely updated, all check-ins, breakfast. Our stay was in an older building… while it was clean there was a musty smell. The room was very dated and the ac was loud… Time to upgrade that building."
Barb 1-night trip
Posted 23 hours ago
The Yankee Inn
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"I liked the balcony overlooking the lake"
Rinat 3-night trip
Posted 3 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 5 days ago
Howard Johnson by Wyndham Lenox

Frequently asked questions

What are some accommodations with pools in Chatham?
Vacation Village in the Berkshires: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Country Inn & Suites by Radisson, Downtown Albany New York: Provides a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Provides buffet, an indoor pool, and complimentary wired internet access. FairBridge Inn Express: Features 3 restaurants, an outdoor pool, and spa services.
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.

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