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Hotels with Swimming Pool in Chatham, New York

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Check availability on Chatham Hotels with Swimming Pool

Tonight
Aug 21 - Aug 22
Tomorrow
Aug 22 - Aug 23
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

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.
P4,161
P4,661 total
includes taxes & fees
Aug 25 - Aug 26
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.
P9,742
P10,882 total
includes taxes & fees
Sep 16 - Sep 17
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.
P7,091
P7,920 total
includes taxes & fees
Sep 20 - Sep 21
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.
P5,833
P7,892 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.
P10,255
P14,518 total
includes taxes & fees
Sep 14 - Sep 15
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.
P4,871
P5,441 total
includes taxes & fees
Sep 1 - Sep 2
Howard Johnson by Wyndham Lenox

7. 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.
P7,214
P9,264 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Club Vacations Oak 'n Spruce Resort

8. 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.
P8,037
P8,978 total
includes taxes & fees
Sep 20 - Sep 21
Hampton Inn & Suites Berkshires-Lenox

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.
P6,937
P7,748 total
includes taxes & fees
Sep 1 - Sep 2
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.
P7,041
P7,816 total
includes taxes & fees
Sep 13 - Sep 14
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Everything was clean and well maintained. Very good included breakfast, close to Tanglewood, the Manor, the Norman Rockwell Museum, Lenox and Stockbridge."
Andrew 2-night trip
Posted 1 hour ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Only real challenge—getting on the hotel wifi was a frustrating challenge! And every time you left your room you had to get on again."
Judith 4-night trip
Posted 2 hours ago
Quality Inn Great Barrington
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We come up to the Berkshires every year for Tanglewood and always stay here. The rooms are always clean and the staff friendly and helpful. The rooms have either a full kitchen or kitchenette so at the very least you can have coffee when you wake-up. The fact that Vacation Village is on Brodie Mountain it's quiet and restful."
William 3-night trip
Posted 1 day ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"…."
Tiago 3-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort

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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