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 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

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 Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

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.
₩191,665
₩214,090 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 modern bathroom with a large mirror, a sink, and a shower.

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.
₩110,743
₩123,700 total
includes taxes & fees
Nov 17 - Nov 18
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 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.

3. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
₩253,507
₩291,533 total
includes taxes & fees
Oct 19 - Oct 20
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 lakeside deck with Adirondack chairs, a canoe, and a wooden railing.
A modern hotel room with a bed, sofa, leather chair, and a small table.

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.
₩359,047
₩412,904 total
includes taxes & fees
Nov 8 - Nov 9
Interlaken Inn & Resort
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 cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

5. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
₩378,260
₩467,228 total
includes taxes & fees
Nov 9 - Nov 10
Prospect Berkshires
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 building with a porch and multiple windows, surrounded by purple flowers.

6. 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.
₩156,107
₩200,458 total
includes taxes & fees
Oct 20 - Oct 21
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A white two-story house with a front door, windows, and a chimney.
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.

7. 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.
₩386,933
₩466,908 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
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 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 rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

8. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
₩202,939
₩227,290 total
includes taxes & fees
Nov 2 - Nov 3
Little Cat Lodge
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.

9. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
₩210,171
₩301,045 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
A large house with a balcony and a grassy yard.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.
A two-story building with a gabled roof and a chimney.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

10. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
₩138,095
₩154,252 total
includes taxes & fees
Oct 19 - Oct 20
The Little Lion
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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

Interlaken Inn & Resort

Interlaken Inn & Resort

10/10 Excellent
"Over eight annual visits to this hotel, it has been a wonderful stay each time."
mary 1-night trip
Posted 16 hours ago
Interlaken Inn & Resort
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"
Hope 1-night trip
Posted 1 day ago
The Red Lion Inn
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8/10 Good
"Property grounds weren’t maintained well. Bathroom faucet was lose."
George 2-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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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