Find Hotels with a Pool in Chatham, NY

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Check availability on Chatham Hotels with a Pool

Tonight
Oct 29 - Oct 30
Tomorrow
Oct 30 - Oct 31
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Top Chatham Hotels with a Pool

Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
  • Outdoor pool
  • Indoor pool
  • Pool umbrellas
8.8 out of 10, Excellent, (2111)
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 ₩101,615
₩129,217 total
includes taxes & fees
Nov 9 - Nov 10
Vacation Village in the Berkshires
Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
  • Indoor pool
8.0 out of 10, Very Good, (930)
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 ₩147,540
₩164,803 total
includes taxes & fees
Nov 2 - Nov 3
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
  • Indoor pool
8.8 out of 10, Excellent, (681)
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 ₩146,108
₩163,203 total
includes taxes & fees
Nov 13 - Nov 14
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool
Element Lenox Berkshires
Element Lenox Berkshires
3.0 star property
  • Indoor pool
9.4 out of 10, Exceptional, (6)
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 ₩193,378
₩216,003 total
includes taxes & fees
Nov 6 - Nov 7
Element Lenox Berkshires
Indoor pool
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
  • Indoor pool
  • Hot tub
9.0 out of 10, Wonderful, (739)
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.
The price is ₩117,800
₩163,583 total
includes taxes & fees
Nov 2 - Nov 3
Berkshire Mountain Lodge
2 indoor pools, 2 outdoor pools, pool umbrellas, sun 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
  • 2 outdoor pools
  • 2 indoor pools
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (771)
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 ₩157,066
₩195,440 total
includes taxes & fees
Oct 30 - Oct 31
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
  • Indoor pool
  • Pool loungers
  • Hot tub
9.0 out of 10, Wonderful, (1021)
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 ₩153,413
₩171,361 total
includes taxes & fees
Nov 2 - Nov 3
The Yankee, Trademark Collection by Wyndham
Exterior
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2.0 star property
  • Outdoor pool
7.6 out of 10, Good, (816)
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 ₩113,162
₩126,398 total
includes taxes & fees
Oct 30 - Oct 31
Howard Johnson by Wyndham Lenox
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion
The Little Lion
3.0 star property
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • Extra beds/cribs
8.6 out of 10, Excellent, (541)
Aquatic adventures beckon with access to a nearby outdoor pool, complementing garden strolls at this cozy Berkshire motel. Nestled close to Norman Rockwell Museum and Ski Butternut, guests praise the helpful staff and comfortable accommodations.
The price is ₩184,783
₩206,403 total
includes taxes & fees
Nov 2 - Nov 3
The Little Lion
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
  • Indoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (1000)
Splash into vacation mode at the indoor pool where comfortable loungers await after exhilarating outdoor adventures. This art deco haven balances active pursuits with relaxation, offering fitness facilities and a delicious free breakfast buffet to fuel Berkshire explorations.
The price is ₩159,286
₩177,923 total
includes taxes & fees
Nov 9 - Nov 10
Hampton Inn & Suites Berkshires-Lenox
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 Chatham Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Good location; reasonable price; very clean and quiet - would definitely return"
Steven 2-night trip
Posted 2 days ago
Vacation Village in the Berkshires

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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: Features 3 restaurants, an outdoor pool, and spa services. The Black Swan Lee - Lenox, an Ascend Collection Hotel: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli.
What is there to see and do in Chatham?
The picturesque setting of Art Omi International Arts Center - Fields Sculpture Park and Kinderhook 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.