A red bridge over a river with snow patches and dry grass.

Find Hotels with a Pool in Canaan, CT

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Check availability on Canaan Hotels with a Pool

Our top choices for Canaan hotels with a pool

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
9.2 out of 10, Wonderful, (937 reviews)
  • cleanliness
    Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
The price is ₩274,918
₩336,169 total
includes taxes & fees
Aug 4 - Aug 5
Holiday Inn Club Vacations Oak n’ Spruce Resort in the 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
Great Barrington
8.8 out of 10, Excellent, (791 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is ₩208,583
₩232,987 total
includes taxes & fees
Aug 13 - Aug 14
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Seasonal outdoor pool

The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.2 out of 10, Wonderful, (1,001 reviews)
The price is ₩433,342
₩498,343 total
includes taxes & fees
Jul 27 - Jul 28
The Litchfield Inn
Indoor pool

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (794 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
The price is ₩288,092
₩321,799 total
includes taxes & fees
Aug 10 - Aug 11
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
M3 Romantic Suite | Living area | 43-inch LCD TV with digital channels, streaming services

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (194 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is ₩230,444
₩265,011 total
includes taxes & fees
Jul 19 - Jul 20
Blackberry River Inn
Seasonal outdoor pool

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (304 reviews)
  • cleanliness
    Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.
The price is ₩358,320
₩412,068 total
includes taxes & fees
Jul 23 - Jul 24
Interlaken Inn & Resort
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (166 reviews)
  • cleanliness
    Serene seasonal outdoor pool retreat nestled near Mohawk Mountain, where pool loungers and umbrellas invite summer relaxation.
The price is ₩313,179
₩360,156 total
includes taxes & fees
Jul 19 - Jul 20
Cornwall Inn and Lodge
Outdoor pool, sun loungers

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is ₩274,401
₩372,635 total
includes taxes & fees
Jul 29 - Jul 30
The Red Lion Inn
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (101 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is ₩326,351
₩365,513 total
includes taxes & fees
Jul 26 - Jul 27
Little Cat Lodge
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (425 reviews)
  • cleanliness
    Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
The price is ₩146,525
₩163,668 total
includes taxes & fees
Jul 29 - Jul 30
Sunset Inn
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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Choose what matters most at hotels with a pool in Canaan

Breakfast included
4 stars

Top Canaan Hotel Reviews

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"Warm welcome from the motel owner and his family. Great access to the town of Great Barrington and convenient to head out to local attractions."
Letitia 3-night trip
Posted 2 hours ago
Monument Mountain Motel

Frequently asked questions

What are some accommodations with pools in Canaan?
The Red Lion Inn: Features 3 restaurants, an outdoor pool, and spa services. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Quality Inn Great Barrington: Offers a sauna, an outdoor pool, and spa services. Quality Inn Lee - Lenox South: Features a sauna, a seasonal outdoor pool, and daily. Prospect Berkshires: Offers a full-service spa, a seasonal outdoor pool, and 3 outdoor tennis courts.
What is there to see and do in Canaan?
Spend some time experiencing the great outdoors at Housatonic River and Edith Scoville Memorial Sanctuary. During your stay, check out sights such as Douglas Library, Lawrence Field, and Connecticut Railroad Historical Museum.
When is the best time to book a hotel with a pool in Canaan?
Taking into account the local weather in Canaan is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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 Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.