Hotels with Swimming Pool, Canaan Connecticut

Q: 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.

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

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Our top choices for Canaan hotels with a pool

The Litchfield Inn

Litchfield

P18,535 total

includes taxes & fees

Jul 21 - Jul 22

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.

P10,579 total

includes taxes & fees

Jul 26 - Jul 27

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.

P13,398 total

includes taxes & fees

Aug 10 - Aug 11

Interlaken Inn & Resort

Lakeville

Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.

P17,124 total

includes taxes & fees

Jul 14 - Jul 15

The Red Lion Inn

Stockbridge

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

P14,839 total

includes taxes & fees

Jul 22 - Jul 23

Little Cat Lodge

Copake Falls

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

P11,740 total

includes taxes & fees

Jul 16 - Jul 17

Blackberry River Inn

Norfolk

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

P11,013 total

includes taxes & fees

Jul 12 - Jul 13

The Little Lion

Great Barrington

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

P7,695 total

includes taxes & fees

Jul 13 - Jul 14

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Choose what matters most at hotels with a pool in Canaan

Breakfast included

4 stars

Top Canaan Hotel Reviews

The Red Lion Inn

10/10 Excellent

"Clean room. Arrived late."

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8/10 Good

"A sweet spot in the Berkshires to “camp” in for an evening or two or three. Who else has your bed made up with crisp white sheets, breakfast in the morning and a warm welcome waiting for you other than your mom? #holidayinnexpress for the win! Thanks!"

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.

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