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

Hotels with Swimming Pools in Canaan

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Check availability on Canaan Hotels with Swimming Pools

Tonight
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Canaan hotels with a pool

A modern hotel lobby with seating areas, tables, and a reception desk.
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.
A hotel reception area with a check-in counter, a Holiday Inn Express sign, and a beverage refrigerator.

1. 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.
S$163
includes taxes & fees
7 Sept - 8 Sept
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 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.
A grand hallway with a chandelier, a staircase, and a table with flowers.

2. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
S$272
includes taxes & fees
30 Aug - 31 Aug
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 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.

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.
S$228
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.

4. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
S$160
includes taxes & fees
1 Sept - 2 Sept
The Little Lion
A backyard with a swimming pool, lounge chairs, and a hot tub.
A covered porch with wicker furniture and hanging flower baskets.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
S$278
includes taxes & fees
23 Sept - 24 Sept
The Red Lion Inn
A living room with a sofa, armchair, coffee table, and a patterned rug.
An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.
A multi-story building with a symmetrical facade, multiple balconies, and a central tower.
A multi-story building with a balcony, a pond with rocks, and a tree.

6. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
S$191
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
A modern hotel room with a bed, sofa, leather chair, and a small table.
A tented area with lush greenery and a dining setup.
A wooden deck with a swing chair and a bench overlooking a lake.

7. 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.
S$314
includes taxes & fees
22 Sept - 23 Sept
Interlaken Inn & Resort
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
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.

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.
S$255
includes taxes & fees
31 Aug - 1 Sept
Little Cat Lodge
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A hotel room with two beds, a chair, and a bedside table with a phone.

9. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.
S$127
includes taxes & fees
28 Sept - 29 Sept
Sunset Inn
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 cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

10. 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.
S$489
includes taxes & fees
1 Sept - 2 Sept
The Old Inn On The Green
View all properties

Choose what matters most at hotels with a pool in Canaan

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Canaan Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent
"staff welcoming place clean."
Ivy 2-night trip
Posted 3 hours ago
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great visit to Stockbridge. Can't think of a better place to stay than the iconic Red Lion Inn."
Daniel 2-night trip
Posted 2 days ago
The Red Lion Inn
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"It was much better than expected. Subtle lighting in the room was a nice touch. Clean and very comfortable bedding and bathroom. Everything in the fitness room was was clean and operational. The breakfast was superb. A very enjoyable stay."
William 1-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Monument Mountain Motel

Monument Mountain Motel

8/10 Good
"Everything was fine except for the spotty WIFI. I was frustrated by how frequent their were interruptions in WIFI service. The WIFI is free but very faulty, as I couldn't get any work done during my stay. I would have preferred to pay for the WIFI just so I could have proper service."
Selwyn 2-night trip
Posted 4 days ago
Monument Mountain Motel
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

10/10 Excellent
"All the staff members I met were cheerful & helpful. I asked for a ground floor room, upon arrival, got a very nice one at no extra charge. I was in the area for a music festival, plan on booking a stay again , next year."
Peter 2-night trip
Posted 12 days ago
Americas Best Value Inn Torrington CT
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

8/10 Good
"We did not use the amenities. We were only there to sleep and for one night, but the staff was friendly and the room was cleanly enough."
Connie 1-night trip
Posted 12 days ago
Travelodge by Wyndham Great Barrington Berkshires

Frequently asked questions

What are some accommodation options with pools in Canaan?
The Red Lion Inn: Features 3 restaurants, an outdoor pool and spa services. Quality Inn Great Barrington: Provides 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Holiday Inn Club Vacations Oak 'n Spruce Resort: Offers a sauna, a seasonal outdoor pool and daily. Quality Inn Lee - Lenox South: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Little Cat Lodge: Offers a full-service spa, a seasonal outdoor pool and a snack bar/deli.
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, visit sights such as Campbell Falls State Park, Lawrence Field and Connecticut Railroad Historical Museum.
When is the best time to book a hotel with a pool in Canaan?
Taking the local weather in 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 Canaan are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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