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

Hotels with Swimming Pools in Canaan

  • 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 Swimming Pools

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

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 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.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
S$151
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A covered outdoor area with stone pillars and a view of a road and green hills.
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.
S$179
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
Pool
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
A spacious hotel lobby with multiple seating areas, large windows, and a television.
Exterior

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.
S$164
includes taxes & fees
4 Nov - 5 Nov
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 spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A garden with wooden Adirondack chairs and a stone pathway.

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
S$151
includes taxes & fees
18 Oct - 19 Oct
Berkshire Mountain Lodge
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern cafe with a counter, seating area, and large windows.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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.
S$141
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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.

6. 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.
S$216
includes taxes & fees
1 Nov - 2 Nov
Element by Marriott Lenox Berkshires
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 hotel patio with outdoor seating and a fire pit.
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

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.
S$183
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Lenox Pittsfield
Outdoor pool
Front of property
Lobby sitting area
Lobby sitting area

8. 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.
S$97
includes taxes & fees
5 Oct - 6 Oct
Berkshire Travel Lodge
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
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.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

9. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
S$113
includes taxes & fees
5 Oct - 6 Oct
Howard Johnson by Wyndham Lenox
Indoor pool
A spacious living room with large windows, a fireplace, and a variety of seating options.
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.
S$137
includes taxes & fees
1 Nov - 2 Nov
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 inn provided a comfortable stay with breakfast included with some healthy options also. The evening staff was very pleasant and helpful. The 2nd floor balcony was tidy and had a good view of the fire pit patio area during the nice fall foliage. The room with two beds was very comfortable and laid out well. The bathroom space had a nice layout too. I will not hesitate to stay at this inn again whenever I am in this area."
Heidi 2-night trip
Posted 2 hours ago
The Yankee Inn
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Great"
Rick 1-night trip
Posted 6 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 swimming 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, visit 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 the local weather in Canaan into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Canaan are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

Explore a world of travel with Expedia