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

Search Hotels with Swimming Pool in Canaan

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Check availability on Canaan Hotels with Swimming Pool

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

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 room with two beds, a desk, a television, and a dresser.

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.
₹13,638
₹15,234 total
includes taxes & fees
2 Nov - 3 Nov
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 bathroom with a large mirror, a sink, and a shower.
A breakfast bar with a variety of food options including cereal, fruit, and yogurt.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

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.
₹8,545
₹9,545 total
includes taxes & fees
12 Nov - 13 Nov
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.

3. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
₹16,756
₹19,269 total
includes taxes & fees
25 Oct - 26 Oct
Blackberry River Inn
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
A wooden deck with a swing chair and a bench overlooking a lake.
A tented area with lush greenery and a dining setup.
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.
₹25,549
₹29,381 total
includes taxes & fees
8 Nov - 9 Nov
Interlaken Inn & Resort
An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A multi-story building with a balcony, a pond with rocks, and a tree.

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.
₹11,108
₹14,264 total
includes taxes & fees
27 Oct - 28 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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 lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
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.
₹23,417
₹29,338 total
includes taxes & fees
9 Nov - 10 Nov
Prospect 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 rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.

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.
₹13,574
₹15,203 total
includes taxes & fees
24 Nov - 25 Nov
Little Cat Lodge
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
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.

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.
₹27,500
₹33,183 total
includes taxes & fees
1 Nov - 2 Nov
The Old Inn On The Green
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 bar with wooden floors and shelves filled with bottles.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

9. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
₹14,955
₹21,422 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
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 two-story building with a gabled roof and a chimney.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.

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.
₹9,815
₹10,963 total
includes taxes & fees
26 Oct - 27 Oct
The Little Lion
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

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 7 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 accommodation options with pools in Canaan?
Quality Inn Great Barrington: Offers 3 restaurants, an outdoor pool and spa services. The Red Lion Inn: Provides 2 indoor swimming pools, 2 outdoor swimming 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, visit 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 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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