TOP Hotels with Pool in Canaan, CT for 2026

Q: What are some accommodation options 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 swimming pools, 2 outdoor swimming pools and a snack bar/deli. Quality Inn Great Barrington : Features a full-service spa, a seasonal outdoor pool and 3 outdoor tennis courts. Days Inn by Wyndham Torrington : Features a full-service spa, a seasonal outdoor pool and a snack bar/deli. Quality Inn Lee - Lenox South : Features buffet, an indoor pool and complimentary high-speed (wired) Internet access.

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Our top choices for Canaan hotels with a pool

The Little Lion

Great Barrington

Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.

฿3,435 total

includes taxes & fees

11 Jun - 12 Jun

The Red Lion Inn

Stockbridge

Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.

฿7,109 total

includes taxes & fees

18 May - 19 May

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.

฿4,484 total

includes taxes & fees

27 May - 28 May

Blackberry River Inn

Norfolk

Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.

฿5,797 total

includes taxes & fees

17 May - 18 May

2 indoor pools, 2 outdoor pools, pool umbrellas, pool loungers

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

South Lee

Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.

฿5,254 total

includes taxes & fees

18 May - 19 May

Little Cat Lodge

Copake Falls

Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.

฿5,515 total

includes taxes & fees

18 May - 19 May

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.

฿6,424 total

includes taxes & fees

18 May - 19 May

The Litchfield Inn

Litchfield

฿9,456 total

includes taxes & fees

19 May - 20 May

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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

10/10 Excellent

"Good"

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"The suite is a great option for a family of five. We have disabled children and found it really easy to get to the pool. The rooms and pool are located in the same building. So we didn’t have to walk through a cold parking lot after swimming. It’s a much better location and quality than a lot of the other similar hotels. it’s already across from a grocery store and local restaurants even a McDonald’s. A great all-around family choice."

Frequently asked questions

What are some accommodation options 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 swimming pools, 2 outdoor swimming pools and a snack bar/deli. Quality Inn Great Barrington: Features a full-service spa, a seasonal outdoor pool and 3 outdoor tennis courts. Days Inn by Wyndham Torrington: Features a full-service spa, a seasonal outdoor pool and a snack bar/deli. Quality Inn Lee - Lenox South: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access.

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, visit 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 the local weather in Canaan into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Canaan are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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