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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Canaan Hotels with a Pool

Tonight
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
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 large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A modern restaurant with wooden flooring, bar area, and seating arrangements.

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
Exterior
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
Bathroom shower

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 a high ceiling, multiple windows, and seating areas.
A spacious lobby with a fireplace, seating area, and a bar.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

4. 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
An indoor swimming pool with clear water, tiled floors, and a blue wall.
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.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.

5. 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 4 - Nov 5
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Outdoor pool
Front of property
Lobby sitting area
Lobby sitting area

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 6 - Oct 7
Berkshire Travel Lodge
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
A hotel patio with outdoor seating and a fire pit.

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 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 modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

8. 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
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.
A bathroom with a white sink, mirror, and toilet.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

9. 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 6 - Oct 7
Howard Johnson by Wyndham Lenox
Indoor pool
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
A spacious living room with large windows, a fireplace, and a variety of seating options.
A spacious living room with a fireplace, comfortable seating, and 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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"The online pre-registration made the check-in process very quick and easy. The condo was spacious and the amenities available in it were convenient, very nice for my quick stay, but also would be great for families staying for an extended period of time. The location is quiet, but close to things to do."
Laura 2-night trip
Posted 1 hour ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"great room and great area"
Ramon 2-night trip
Posted 2 hours ago
Jiminy Peak Mountain Resort
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great staff, heated bathroom floors."
Ellen 3-night trip
Posted 3 hours ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The cleaning staff were friendly and helpful!"
Mayra 2-night trip
Posted 18 hours ago
Quality Inn Great Barrington

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.

Explore a world of travel with Expedia