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

Find Hotels with a Pool in Canaan, NY

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Check availability on Canaan Hotels with a Pool

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
₩141,489
₩158,043 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A modern bathroom with a wooden vanity, a toilet, and two framed pictures on the wall.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.

2. 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.
₩147,342
₩164,582 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Berkshires-Lenox
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 large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A covered outdoor area with stone pillars and a view of a road and green hills.

3. 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 center.
₩168,788
₩188,537 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A modern reception area with a green textured wall, a reception desk, and a coffee machine.

4. 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.
₩171,839
₩191,942 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
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, seating area, and a bar.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
₩115,190
₩158,686 total
includes taxes & fees
Nov 9 - Nov 10
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 hotel room with a bed, a desk, a chair, a TV, and a wardrobe.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

6. 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.
₩132,145
₩147,605 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
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.

7. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
₩105,449
₩117,787 total
includes taxes & fees
Oct 22 - Oct 23
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 modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

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.
₩192,156
₩214,639 total
includes taxes & fees
Nov 8 - Nov 9
Element by Marriott Lenox Berkshires
Outdoor pool
Front of property
Exterior
Lobby sitting area

9. 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.
₩90,086
₩100,898 total
includes taxes & fees
Oct 19 - Oct 20
Berkshire Travel Lodge
Indoor pool
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.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

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.
₩107,241
₩134,430 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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"This is a gem of a small hotel/motel. Super comfortable rooms, updated bathrooms, and well done self serve breakfast included. Also has an indoor pool and an outdoor pool during the season. And a very nice hiking trail off of the back. An excellent change from the Run of the middle courtyard Marriott!"
Kimberly 2-night trip
Posted 13 hours ago
The Yankee Inn
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

8/10 Good
"The room was pretty decent for the price point - everything was clean, the beds were super comfortable, and the room was spacious. I wasn’t very impressed with the staff we interacted with - the woman working the front desk when I checked in didn’t acknowledge me (or even look up from what she was doing) for an awkward amount of time even though I was standing directly in front of her. We wished the room would have had extra linens, a blanket, and pillows for the pull-out bed so we didn’t have to go get them ourselves. We did ask for a blanket for the pull-out bed and weren’t given one. Not a huge deal, but not super helpful or friendly service. The breakfast was nothing spectacular but probably pretty standard. It did the trick and I’m not one to complain about a complimentary meal."
Kristen 1-night trip
Posted 13 hours ago
Comfort Inn & Suites East Greenbush - Albany
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We had a wonderful family stay at Vacation Village in the Berkshires! We traveled with our children and their grandmothers, and it was such a special opportunity to make memories together. Our accommodation felt like two apartments in one, with plenty of space for everyone. We loved the layout and the beautiful views, especially with the fall colors surrounding us. It was lovely to enjoy the scenery right where we were staying. The location was a great base for exploring the Berkshires, and we felt we got excellent value for the price. This trip was very special for our family, and we would love to come back. Highly recommend it for a family getaway!"
Viviane 2-night trip
Posted 15 hours ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

8/10 Good
"I enjoyed my stay, lovely little town. The Inn is beginning to show some signs of wear. A broken tile (baseboard) by the tub. However, staff pleasant and helpful. Excellent restaurants."
Nan 1-night trip
Posted 15 hours ago
The Red Lion Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Our room was nice and clean. The suite is perfect. Can fix a cup of tea or a meal, everything you need just bring your food. A restaurant on site if you don't want to cook. Bed was comfortable with crisp white linens."
Anna 2-night trip
Posted 3 days ago
Jiminy Peak Mountain Resort

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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