A calm lake with reflections of the sky and trees, surrounded by lush greenery and hills.

Find Hotels with a Pool in Canaan, NY from CA $108

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Check availability on Canaan Hotels with a Pool

Tonight
Oct 4 - Oct 5
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Oct 5 - Oct 6
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Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Canaan hotels with a pool

A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
CA $140
CA $156 total
includes taxes & fees
Oct 19 - Oct 20
The Yankee Inn
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A covered outdoor area with stone pillars and a view of a road and green hills.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

2. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness centre.
CA $179
CA $200 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
Pool
Bathroom shower
Exterior
A spacious hotel lobby with multiple seating areas, large windows, and a television.

3. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
CA $164
CA $183 total
includes taxes & fees
Nov 4 - Nov 5
Hampton Inn & Suites Berkshires-Lenox
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A modern cafe with a counter, seating area, and large windows.

4. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
  • Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
CA $147
CA $164 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
CA $121
CA $167 total
includes taxes & fees
Oct 18 - Oct 19
Berkshire Mountain Lodge
Outdoor pool
Lobby sitting area
Lobby sitting area
Exterior

6. Berkshire Travel Lodge

Berkshire Travel Lodge
Austerlitz
  • Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
CA $96
CA $108 total
includes taxes & fees
Oct 5 - Oct 6
Berkshire Travel Lodge
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A spacious living room with a large sofa, a coffee table, and a fireplace.

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
  • Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
CA $182
CA $204 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A bathroom with a white sink, mirror, and toilet.

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
CA $113
CA $126 total
includes taxes & fees
Oct 5 - Oct 6
Howard Johnson by Wyndham Lenox
A large indoor swimming pool with clear blue water, surrounded by white lounge chairs and a few potted plants.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

9. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
  • Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
CA $215
CA $240 total
includes taxes & fees
Nov 1 - Nov 2
Element by Marriott Lenox Berkshires
Indoor pool
A spacious living room with a fireplace, comfortable seating, and large windows.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

10. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
  • Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
CA $123
CA $153 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
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

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"It was a great stay. Very clean rooms and very nice location. Would recommend"
Sean 2-night trip
Posted 11 hours ago
Comfort Inn & Suites East Greenbush - Albany

Frequently asked questions

What are some hotels with pools in Canaan?
Vacation Village in the Berkshires: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. Quality Inn Great Barrington: Features a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn: Offers a steam room, 3 indoor pools, and spa services. Pocketbook Hotel and Bath: Offers 3 restaurants, an outdoor pool, and spa services.
What is there to see and do in Canaan?
The picturesque setting of Queechy Lake showcases the area's natural beauty. During your stay, check out sights such as Hollow FIelds Reserve, Hand Hollow State Forest, and Bates Memorial State Park.
When is the best time to book a hotel with a pool in Canaan?
Taking into account the local weather in Canaan can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°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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