Hotels with Swimming Pool in Chatham, New York

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Chatham Hotels with Swimming Pool

Next weekend
In two weeks

Top Chatham Hotels with Swimming Pool

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Indoor pool
8.0 out of 10, Very Good, (962)
Swimmers splash in the pristine indoor pool from 7 AM to 9 PM, complemented by an on-site health club for complete wellness. Hiking trails and skiing opportunities nearby make this centrally located hotel an ideal family-friendly retreat.
The price is P5,272
P5,889 total
includes taxes & fees
Nov 29 - Nov 30
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.8 out of 10, Exceptional, (11)
Swimming enthusiasts appreciate the serene indoor pool that provides year-round aquatic enjoyment regardless of weather. After energizing laps, guests gather at the outdoor firepit or enjoy a complimentary manager's reception before retreating to individually furnished rooms.
The price is P7,709
P8,610 total
includes taxes & fees
Dec 11 - Dec 12
Element Lenox Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
  • Outdoor pool
  • Indoor pool
  • Pool umbrellas
8.8 out of 10, Excellent, (2141)
Mountain-view relaxation awaits at the indoor and outdoor pools after exploring Berkshire trails. Families appreciate the children's pool, playground, and game room, while skiers love the direct access to Jiminy Peak slopes.
The price is P4,358
P5,513 total
includes taxes & fees
Nov 23 - Nov 24
Vacation Village in the Berkshires

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Indoor pool
  • Pool loungers
  • Hot tub
9.2 out of 10, Wonderful, (1006)
Shimmering waters beckon at dual pool options, where indoor relaxation meets seasonal outdoor splendor. After exploring nearby Bousquet Ski Area, guests unwind in the rejuvenating hot tub while mountain vistas provide a stunning backdrop for aquatic serenity.
The price is P4,366
P4,877 total
includes taxes & fees
Dec 14 - Dec 15
The Yankee, Trademark Collection by Wyndham

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
  • Indoor pool
8.8 out of 10, Excellent, (696)
Splash into the warm, pristine indoor pool after exploring nearby hiking trails or skiing at Butternut. Modern rooms with premium bedding await, while a complimentary breakfast buffet energizes adventures in Great Barrington's vibrant surroundings.
The price is P6,319
P7,058 total
includes taxes & fees
Nov 25 - Nov 26
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Outdoor pool
7.6 out of 10, Good, (825)
Sparkling waters beckon at the inviting outdoor pool, a refreshing retreat after exploring nearby Tanglewood Music Center. Deep soaking bathtubs and hydromassage showers in clean, spacious rooms complement this conveniently located getaway.
The price is P4,649
P5,192 total
includes taxes & fees
Nov 24 - Nov 25
Howard Johnson by Wyndham Lenox

Sunset Inn

2.0 star property
Lee
  • Near the beach
7.6 out of 10, Good, (410)
Mountain recreation surrounds this quiet getaway featuring a refreshing seasonal pool open from August. After swimming, guests appreciate clean, comfortable rooms with mini fridges before exploring nearby skiing and hiking trails.
The price is P5,315
P5,937 total
includes taxes & fees
Dec 2 - Dec 3
Sunset Inn

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
  • Indoor pool
9.2 out of 10, Wonderful, (657)
Sparkling waters await in the pristine indoor swimming pool, complemented by a modern fitness center for complete rejuvenation. Nearby Tanglewood Music Center offers cultural enrichment, while Jae's Asian Fusion restaurant provides delicious dining options.
The price is P6,567
P7,335 total
includes taxes & fees
Dec 14 - Dec 15
Hilton Garden Inn Lenox Pittsfield

Berkshire Mountain Lodge

3.0 star property
Pittsfield
  • Indoor pool
  • Hot tub
9.0 out of 10, Wonderful, (763)
Plunge into the pristine indoor pool after exploring hiking trails or nearby Tanglewood Music Center. Sun loungers invite relaxation while the hot tub soothes tired muscles. Beyond aquatic pleasures, this lodge offers fitness facilities and an arcade room.
Berkshire Mountain Lodge

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

3.5 star property
South Lee
  • 2 outdoor pools
  • 2 indoor pools
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (787)
Swimming enthusiasts rejoice at this four-pool paradise nestled in the Berkshires. Families appreciate the well-maintained waters complemented by sun loungers, umbrellas, and refreshing poolside drinks, creating memorable mountain getaways year-round.
The price is P6,267
P7,822 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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.

Top Chatham Hotel Reviews

Frequently asked questions

What are some accommodations with pools in 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. Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Provides a health club, an indoor pool, and complimentary wired internet access. Berkshires Untold: Offers 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn: Features buffet, an indoor pool, and free self parking.
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.