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

Find Hotels with a Pool in Canaan, CT

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Check availability on Canaan Hotels with a Pool

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

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 lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A hotel room with two beds, a desk, a television, and a dresser.
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

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

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.
￥22,534
￥25,170 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.
A modern hotel lobby with seating areas, tables, and a reception desk.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.
A breakfast bar with a variety of food options including cereal, fruit, and yogurt.

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

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.
￥14,118
￥15,770 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Express Hotel & Suites Great Barrington by IHG
An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.
A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.
A grand hallway with a chandelier, a staircase, and a table with flowers.
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

3. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
￥28,017
￥32,219 total
includes taxes & fees
Oct 25 - Oct 26
Blackberry River Inn
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
A tented area with lush greenery and a dining setup.
A wooden deck with a swing chair and a bench overlooking a lake.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

4. Interlaken Inn & Resort

Interlaken Inn & Resort
Lakeville
  • Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.
￥42,214
￥48,546 total
includes taxes & fees
Nov 8 - Nov 9
Interlaken Inn & Resort
An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.
A multi-story building with a balcony, a pond with rocks, and a tree.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
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

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.
￥18,354
￥23,568 total
includes taxes & fees
Oct 27 - Oct 28
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A poolside area with lounge chairs and a pool.
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.
A wooden table with a green chair and a yellow vase with flowers.

6. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
￥38,692
￥48,475 total
includes taxes & fees
Nov 9 - Nov 10
Prospect Berkshires
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
A house with a stone patio and wooden stools.
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.

7. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
￥22,667
￥25,388 total
includes taxes & fees
Nov 24 - Nov 25
Little Cat Lodge
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 white two-story house with a front door, windows, and a chimney.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

8. The Old Inn On The Green

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.
￥45,492
￥54,895 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
A large house with a balcony and a grassy yard.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.

9. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
￥16,236
￥18,136 total
includes taxes & fees
Oct 25 - Oct 26
The Little Lion
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.

10. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
￥24,710
￥35,395 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
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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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"The hotel was clean and pleasant. Staff members were courteous and helpful! Very satisfied with our stay and will consider a future stay here!"
Anne Marie 2-night trip
Posted 9 hours ago
Quality Inn Great Barrington
Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"A dream to park outside my door! Very simple, clean, and comfortable room. Quiet! Wonderful people and an excellent location. My go to."
Tracy 6-night trip
Posted 1 day ago
Monument Mountain Motel
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Absolutely great location! An older property- the lobby and hallways seemed dark and aging (yes it’s historic). Our room was surprisingly cheerful! I’d stay here again!!"
carole 1-night trip
Posted 1 day ago
The Red Lion Inn

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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