Find Hotels with a Pool in Canaan, CT

  • 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

Our top choices for Canaan hotels with a pool

Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
"The pool and hot tube were open, maybe bring a swimsuit if you are up for a soak in the hot tub on a cold snowy day or night."
United States
Judith Pauline
The price is AED 567
AED 797 total
includes taxes & fees
31 May - 1 Jun
The Red Lion Inn
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, (766 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
"The pool was very clean."
United States
Alessandro
The price is AED 455
AED 509 total
includes taxes & fees
1 Jun - 2 Jun
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
"we loved using the pool at the beautiful Red Lion"
United States
Lisa
The price is AED 349
AED 390 total
includes taxes & fees
11 Jun - 12 Jun
The Little Lion
Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (181 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
"Pool was perfect."
United States
Diane
The price is AED 560
AED 645 total
includes taxes & fees
24 May - 25 May
Blackberry River Inn
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, (898 reviews)
  • cleanliness
    Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
"Large pool, hot tub and saunas on site."
United States
Marcella
The price is AED 426
AED 548 total
includes taxes & fees
25 May - 26 May
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (780 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
"Nice outdoor seating areas, big pool, clean nicely appointed toom"
United States
Jennifer
The price is AED 621
AED 694 total
includes taxes & fees
28 May - 29 May
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (78 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
"We look forward to returning and using the pool."
United States
Evelyn
The price is AED 559
AED 626 total
includes taxes & fees
27 May - 28 May
Little Cat Lodge
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (413 reviews)
  • cleanliness
    Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
"I like the fact that there is a pool and its clean."
United States
pilar
The price is AED 392
AED 438 total
includes taxes & fees
26 May - 27 May
Sunset Inn
Library

The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.2 out of 10, Wonderful, (995 reviews)
"Wonderful Stay. The Garden Suite was Stunning. The Fireplace gave a warm glow and the soaking tub with bath salts was Divine after a long day. I enjoyed reading and relaxing in the Wicker Nest Chair in my complimentary bath robe…EVERYTHING was Perfect and the Staff were AMAZING!!! Thank you. "
United States
Scarlett
The price is AED 998
AED 1,148 total
includes taxes & fees
31 May - 1 Jun
The Litchfield Inn
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, (161 reviews)
  • cleanliness
    Serene seasonal outdoor pool retreat nestled near Mohawk Mountain, where pool loungers and umbrellas invite summer relaxation.
"Enjoyed relaxing g at the pool and in my room."
United States
Susan
The price is AED 777
AED 894 total
includes taxes & fees
26 May - 27 May
Cornwall Inn and Lodge
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

Choose what matters most at hotels with a pool in Canaan

Breakfast included
4 stars

Top Canaan Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The front porch. The dining rooms. The staff. Everything was perfect from the time we entered until the time we departed."
Nicholas 1-night trip
Posted 2 hours ago
The Red Lion Inn

Explore a world of travel with Expedia

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 buffet, an indoor pool, and complimentary wired internet access. Americas Best Value Inn Torrington CT: Features a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Days Inn by Wyndham Torrington: Features 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 Beckley Furnace Industrial Park. During your stay, check out sights such as Campbell Falls State Park, C H Pease Museum, and North Canaan Town Hall.
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.