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

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Check availability on Canaan Hotels with Pool

Tonight
18 Oct - 19 Oct
Tomorrow
19 Oct - 20 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

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 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.
฿3,543
฿3,957 total
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 large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

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.
฿4,198
฿4,690 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
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.

3. 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.
฿3,175
฿3,547 total
includes taxes & fees
17 Nov - 18 Nov
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, seating area, and a bar.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
฿2,892
฿3,977 total
includes taxes & fees
10 Nov - 11 Nov
Berkshire Mountain 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 gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

5. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
฿2,641
฿2,949 total
includes taxes & fees
19 Oct - 20 Oct
Howard Johnson by Wyndham Lenox
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

6. 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.
฿4,801
฿5,363 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A large indoor swimming pool with clear blue water, surrounded by white lounge chairs and a few potted plants.
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.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

7. 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.
฿4,512
฿5,040 total
includes taxes & fees
8 Nov - 9 Nov
Element by Marriott Lenox Berkshires
A hot tub with a tiled floor and a metal ladder.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A bathroom with a large mirror, a sink, and a towel rack.

8. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
  • Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
฿3,510
฿3,920 total
includes taxes & fees
7 Nov - 8 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool
A spacious living room with a fireplace, comfortable seating, and large windows.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

9. 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.
฿2,685
฿3,366 total
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
Outdoor pool
Lobby sitting area
Lobby sitting area
Front of property

10. 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.
฿2,256
฿2,527 total
includes taxes & fees
21 Oct - 22 Oct
Berkshire Travel Lodge
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

8/10 Good
"Sometimes staff is not available, pay more attention to gym, also rooms were not serviced and when service was requested the linens were not changed"
Andrew 5-night trip
Posted 10 hours ago
Comfort Inn & Suites East Greenbush - Albany
Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"This was our 10 yr celebrating my girlfriend’s birthday at Vacation Village. It’s always a nice escape in the fall season. We usually get the larger “A” rooms as we want the in room jacuzzi. This time I got the same larger room but it was a “C” unit. It was a bit smaller all around. And the bed was a small queen instead of the larger king bed. Overall nice. But I will make sure to ask for an “A” unit next year. It is a great location right across the street from Jiminey Peak."
Robert 2-night trip
Posted 13 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Well run and worth it!Hot tub closed for maintenance."
Vincent 1-night trip
Posted 20 hours ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"
Hope 1-night trip
Posted 1 day ago
The Red Lion Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."
Christopher 3-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 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.

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