Hotels with Swimming Pool, Canaan Connecticut

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

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A hotel room with two beds, a desk, a television, and a dresser.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

1. 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.

P9,016

P10,071 total

includes taxes & fees

Nov 2 - Nov 3

An indoor swimming pool with clear lane markings, a poolside area with lounge chairs, and large windows allowing natural light.

A breakfast area with a counter, coffee machine, and a display of pastries.

A modern hotel lobby with seating areas, tables, and a reception desk.

A hotel room with two beds, a desk, a TV, and a window with curtains.

2. 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.

P6,214

P6,941 total

includes taxes & fees

Nov 8 - Nov 9

An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.

A bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

3. Blackberry River Inn

Norfolk

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

P9,414

P10,827 total

includes taxes & fees

Oct 13 - Oct 14

A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.

A wooden deck with a swing chair and a bench overlooking a lake.

A modern hotel room with a bed, sofa, leather chair, and a small table.

A tented area with lush greenery and a dining setup.

4. Interlaken Inn & Resort

Lakeville

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

P13,507

P15,533 total

includes taxes & fees

Nov 8 - Nov 9

A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

A living room with a sofa, armchair, coffee table, and a patterned rug.

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

5. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

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

P7,343

P9,429 total

includes taxes & fees

Oct 12 - Oct 13

A dining area with round tables set for two, a fireplace, and a mural on the wall.

A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.

A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

6. The Old Inn On The Green

Great Barrington

Dive into summer luxury at this historic inn's outdoor pool surrounded by garden serenity and natural wonders.

P18,201

P21,963 total

includes taxes & fees

Nov 1 - Nov 2

A poolside area with lounge chairs and a pool.

A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

A wooden deck with a dog silhouette against a backdrop of autumn foliage.

A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

7. Prospect Berkshires

Egremont

Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.

P19,488

P23,871 total

includes taxes & fees

Nov 2 - Nov 3

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

8. Little Cat Lodge

Copake Falls

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

P9,546

P10,692 total

includes taxes & fees

Nov 2 - Nov 3

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Choose what matters most at hotels with a pool in Canaan

Breakfast included

4 stars

5 stars

Hot tub

Spa

Top Canaan Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Clean room, very friendly and accommodating staff and free parking"

The Red Lion Inn

8/10 Good

"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"

Monument Mountain Motel

10/10 Excellent

"Super clean and cozy and safe"

Quality Inn Great Barrington

8/10 Good

"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."

Interlaken Inn & Resort

10/10 Excellent

"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."

Frequently asked questions

What are some accommodations with pools in Canaan?

Quality Inn Great Barrington: Offers 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Holiday Inn Club Vacations Oak 'n Spruce Resort: Features a sauna, an outdoor pool, and spa services. Prospect Berkshires: Features a full-service spa, a seasonal outdoor pool, and a snack bar/deli. The Abner Hotel: Offers a sauna, a seasonal outdoor pool, and daily.

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 Lawrence Field, Connecticut Railroad Historical Museum, and Douglas Library.

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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Check availability on Canaan Hotels with Swimming Pool

Our top choices for Canaan hotels with a pool

1. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires