TOP Hotels with Pool in North Canaan, CT for 2026

Q: What are some accommodation options with pools in North Canaan?

Blackberry River Inn : Features cooked-to-order, a seasonal outdoor pool and free self parking. Locust Tree Bed and Breakfast LLC : Provides 3 restaurants, an outdoor pool and spa services. The Red Lion Inn : Offers 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Quality Inn Great Barrington : Provides a full-service spa, a seasonal outdoor pool and a snack bar/deli. Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG : Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access.

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Our top choices for North Canaan hotels with a pool

M3 Romantic Suite | Living area | 43-inch LCD TV with digital channels, streaming services

Blackberry River Inn

Norfolk

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

฿5,829 total

includes taxes & fees

21 Jun - 22 Jun

The Little Lion

Great Barrington

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

฿3,200 total

includes taxes & fees

21 Jun - 22 Jun

The Red Lion Inn

Stockbridge

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

฿7,098 total

includes taxes & fees

1 Jul - 2 Jul

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.

฿4,982 total

includes taxes & fees

23 Jun - 24 Jun

Little Cat Lodge

Copake Falls

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

฿5,545 total

includes taxes & fees

24 Jun - 25 Jun

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.

฿5,349 total

includes taxes & fees

22 Jun - 23 Jun

The Litchfield Inn

Litchfield

฿10,175 total

includes taxes & fees

21 Jun - 22 Jun

Sunset Inn

Lee

Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.

฿4,000 total

includes taxes & fees

13 Jul - 14 Jul

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Choose what matters most at hotels with a pool in North Canaan

Breakfast included

4 stars

Top North Canaan Hotel Reviews

Monument Mountain Motel

10/10 Excellent

"The owners are very pleasant The room was very clean The shower was very hot The AC was very cold"

The Red Lion Inn

10/10 Excellent

"The Red Lion Inn has so much history and character, it was a wonderful Experience to say the least. With modern amenities, it still Managed to keep its old world charm Food at the Wolf Den Tavern offered some of the best clam chowder I have ever had Enjoyed the hot tub but both hot tub and pool were difficult getting in and out of for someone with mobility issues like me Breakfast in the main dining room was also wonderful with very pleasant staff Upon check in, the only employee at the registration desk was on the phone with a customer for a good 15-20 minutes while the line behind me were all waiting to check in. Since check in time is 4:00, and we were there at 4:30 it seems like there should be more than one employee checking in customers Overall a wonderful stay. One that I would happily do again"

Frequently asked questions

What are some accommodation options with pools in North Canaan?

Blackberry River Inn: Features cooked-to-order, a seasonal outdoor pool and free self parking. Locust Tree Bed and Breakfast LLC: Provides 3 restaurants, an outdoor pool and spa services. The Red Lion Inn: Offers 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Quality Inn Great Barrington: Provides a full-service spa, a seasonal outdoor pool and a snack bar/deli. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access.

What is there to see and do in North Canaan?

The picturesque setting of Housatonic River and Edith Scoville Memorial Sanctuary showcase the area's natural beauty. During your stay, visit sights such as Campbell Falls State Park, Lawrence Field and Connecticut Railroad Historical Museum.

When is the best time to book a hotel with a pool in North Canaan?

Taking the local weather in North 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 North Canaan are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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