Photo by Robin/Loving Life

Find Hotels with a Pool in Canaan, NY

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Canaan Hotels with a Pool

Tonight
Nov 28 - Nov 29
Tomorrow
Nov 29 - Nov 30
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Top Canaan Hotels with a Pool

Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Indoor pool
  • Pool loungers
  • Hot tub
9.2 out of 10, Wonderful, (1011)
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 ₩91,367
₩102,057 total
includes taxes & fees
Dec 7 - Dec 8
The Yankee, Trademark Collection by Wyndham
Indoor pool
Element Lenox Berkshires

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 ₩191,581
₩213,995 total
includes taxes & fees
Dec 11 - Dec 12
Element Lenox Berkshires
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
  • Indoor pool
  • Hot tub
9.2 out of 10, Wonderful, (63)
Plunge into the indoor pool open from 8:00 AM to 10:00 PM after exploring nearby Tanglewood Music Center. Soothing hot tub sessions complement winter activities like cross-country skiing, while attentive staff ensure a refreshingly clean, well-maintained aquatic retreat.
The price is ₩139,225
₩155,513 total
includes taxes & fees
Dec 7 - Dec 8
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
  • Outdoor pool
  • Indoor pool
  • Pool umbrellas
8.8 out of 10, Excellent, (2149)
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 ₩108,297
₩137,011 total
includes taxes & fees
Nov 30 - Dec 1
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
Pittsfield
  • Indoor pool
8.0 out of 10, Very Good, (973)
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 ₩135,833
₩151,725 total
includes taxes & fees
Dec 1 - Dec 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Seasonal outdoor pool
The Springs Motel

The Springs Motel

2.0 star property
New Ashford
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Microwave
9.2 out of 10, Wonderful, (87)
Surrounded by mountain views, the seasonal outdoor pool offers summer relaxation with comfortable lounge chairs and hangout spots. Guests love the well-appointed rooms, friendly staff, and outdoor entertainment areas featuring firepits and charcoal grills.
The price is ₩176,635
₩193,769 total
includes taxes & fees
Nov 30 - Dec 1
The Springs Motel
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
South Lee
  • 2 outdoor pools
  • 2 indoor pools
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (790)
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 ₩155,751
₩194,390 total
includes taxes & fees
Dec 1 - Dec 2
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Outdoor pool
7.6 out of 10, Good, (826)
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 ₩115,534
₩129,047 total
includes taxes & fees
Nov 30 - Dec 1
Howard Johnson by Wyndham Lenox
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
Lenox
  • Indoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (1003)
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 ₩162,625
₩181,653 total
includes taxes & fees
Dec 7 - Dec 8
Hampton Inn & Suites Berkshires-Lenox
Indoor pool
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.2 out of 10, Wonderful, (587)
Sparkling waters welcome swimmers at the inviting indoor pool, complementing days spent exploring nearby Tanglewood Music Center and Kennedy Park. Staff members earn consistent praise for their attentive service at this comfortable Lenox retreat.
The price is ₩185,731
₩207,461 total
includes taxes & fees
Nov 30 - Dec 1
Courtyard by Marriott Lenox Berkshires
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 Canaan Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Good waffles"
Dana 1-night trip
Posted 3 days ago
Comfort Inn & Suites East Greenbush - Albany

Explore a world of travel with Expedia

Frequently asked questions

What are some hotels with pools in Canaan?
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 buffet, an indoor pool, and free self parking. Comfort Inn & Suites East Greenbush - Albany: Features 3 restaurants, an outdoor pool, and spa services.
What is there to see and do in Canaan?
The picturesque setting of Queechy Lake showcases the area's natural beauty. During your stay, check out sights such as Hollow FIelds Reserve, Hand Hollow State Forest, and Bates Memorial State Park.
When is the best time to book a hotel with a pool in Canaan?
Taking into account the local weather in Canaan 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 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.