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North Canaan Hotel Guide - Hotels with Pool in North Canaan, Connecticut

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Check availability on North Canaan Hotels with Pool

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

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

1. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
€195
includes taxes & fees
21 Oct - 22 Oct
Blackberry River Inn
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 modern bathroom with a large mirror, a sink, and a shower.
A breakfast area with a counter, coffee machine, and a display of pastries.

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.
€83
includes taxes & fees
18 Nov - 19 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 hotel room with two beds, a desk, a television, and a dresser.

3. 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.
€143
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

4. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
€152
includes taxes & fees
2 Nov - 3 Nov
Little Cat Lodge
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 hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

5. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
€103
includes taxes & fees
21 Oct - 22 Oct
The Little Lion
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 room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A white two-story house with a front door, windows, and a chimney.

6. 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.
€312
includes taxes & fees
1 Nov - 2 Nov
The Old Inn On The Green
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 building with a porch and multiple windows, surrounded by purple flowers.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

7. 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.
€134
includes taxes & fees
27 Oct - 28 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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 large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.

8. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
€201
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.
A tented area with lush greenery and a dining setup.
A modern hotel room with a bed, sofa, leather chair, and a small table.

9. 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.
€276
includes taxes & fees
8 Nov - 9 Nov
Interlaken Inn & Resort
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 cabin with a bed, a chair, and a table by a large window overlooking a lake.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.

10. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
€312
includes taxes & fees
9 Nov - 10 Nov
Prospect Berkshires
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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 1 day 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 accommodation options 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 swimming pools, 2 outdoor swimming 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, visit 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 the local weather in North Canaan into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in North Canaan are January, March, February and November, with each month seeing an average of 18 cm of snowfall.