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Hotels with Swimming Pool in North Canaan, Connecticut

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Check availability on North Canaan Hotels with Swimming Pool

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for North Canaan hotels with a pool

An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.
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.
A bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.

1. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
P11,966
P13,761 total
includes taxes & fees
Nov 2 - Nov 3
Blackberry River Inn
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
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.
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

2. 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.
P9,061
P10,121 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 hotel room with two beds, a desk, a TV, and a window with curtains.
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.

3. 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.
P5,235
P5,848 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 wooden deck with a swing chair and a bench overlooking a lake.

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.
P16,974
P19,520 total
includes taxes & fees
Nov 8 - Nov 9
Interlaken Inn & Resort
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
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.

5. 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.
P18,264
P22,039 total
includes taxes & fees
Nov 2 - Nov 3
The Old Inn On The Green
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A house with a stone patio and wooden stools.
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.

6. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
P9,594
P10,745 total
includes taxes & fees
Nov 2 - Nov 3
Little Cat Lodge
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

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
P17,882
P22,088 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 hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A building with a porch and multiple windows, surrounded by purple flowers.

8. 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.
P7,369
P9,462 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A poolside area with lounge chairs and umbrellas, a pool, and a person relaxing.
A spacious hotel room with a large bed, a sitting area with a sofa and chairs, a dining table, and a kitchen area with cabinets and a coffee machine.
A room with a hanging rattan chair, a wooden sofa, a small round table, and a ceiling fan. Large windows provide views of greenery outside.
A stone building with a wooden staircase and a garden with white flowers.

9. Troutbeck

Troutbeck
Amenia
P39,199
P46,867 total
includes taxes & fees
Oct 21 - Oct 22
Troutbeck
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A bar with wooden floors and shelves filled with bottles.
A covered porch with wicker furniture and hanging flower baskets.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

10. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
P9,936
P14,232 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
View all properties

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

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top North Canaan Hotel Reviews

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"Very clean!!! Bathroom was bright. Great value!"
c 1-night trip
Posted 23 hours ago
Monument Mountain Motel
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 2 days ago
Quality Inn Great Barrington
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 3 days ago
Interlaken Inn & Resort

Frequently asked questions

What are some accommodations 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: Features 3 restaurants, an outdoor pool, and spa services. Quality Inn Great Barrington: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Red Lion Inn: Features a sauna, an outdoor pool, and spa services. Holiday Inn Club Vacations Oak 'n Spruce Resort: Provides a full-service spa, a seasonal outdoor pool, and a snack bar/deli.
What is there to see and do in North Canaan?
Spend some time experiencing the great outdoors at Housatonic River. During your stay, check out sights such as Lawrence Field, Edith Scoville Memorial Sanctuary, and Connecticut Railroad Historical Museum.
When is the best time to book a hotel with a pool in North Canaan?
Taking into account the local weather in North 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 North Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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