Hotels with Swimming Pool in Canaan, Connecticut

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Check availability on Canaan Hotels with Swimming 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 price is P7,969
P11,557 total
includes taxes & fees
Apr 12 - Apr 13
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, (754 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is P6,359
P7,103 total
includes taxes & fees
Apr 29 - Apr 30
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, (555 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is P6,537
P7,302 total
includes taxes & fees
Apr 12 - Apr 13
The Little Lion
Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (173 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is P9,253
P10,641 total
includes taxes & fees
Apr 12 - Apr 13
Blackberry River 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, (777 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
The price is P9,033
P10,090 total
includes taxes & fees
Apr 26 - Apr 27
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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
9.0 out of 10, Wonderful, (862 reviews)
  • cleanliness
    Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
The price is P6,686
P8,630 total
includes taxes & fees
Apr 13 - Apr 14
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
  • cleanliness
    Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
The price is P5,943
P6,638 total
includes taxes & fees
Apr 13 - Apr 14
Sunset Inn
Library

The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.0 out of 10, Wonderful, (978 reviews)
The price is P15,070
P17,331 total
includes taxes & fees
Apr 12 - Apr 13
The Litchfield Inn
Seasonal outdoor pool

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (291 reviews)
  • cleanliness
    Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.
The price is P13,318
P15,315 total
includes taxes & fees
Apr 16 - Apr 17
Interlaken Inn & Resort
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (75 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is P10,109
P11,322 total
includes taxes & fees
Apr 12 - Apr 13
Little Cat 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.
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Choose what matters most at hotels with a pool in Canaan

Breakfast included
4 stars

Top Canaan Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent
"Smooth as silk - staff was beyond exceptional. Gym was under construction but can’t fault them for that. Pool was working! It really was perfect. Thank you!"
Martina 1-night trip
Posted 2 hours ago
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Frequently asked questions

What are some accommodations with pools in Canaan?
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Hotel located near National Shrine of the Divine Mercy. Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Red Lion Inn: Hotel, 15-minute walk from National Shrine of the Divine Mercy. Offers 3 restaurants, an outdoor pool, and spa services. Quality Inn Great Barrington: Features buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express Hotel & Suites Great Barrington by IHG: Features a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Days Inn by Wyndham Torrington: Offers full, an indoor pool, and complimentary wired internet access.
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 C H Pease Museum, North Canaan Town Hall, and Campbell Falls State Park.
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.

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