Photo by Robin/Loving Life

Search Hotels with Pool 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 prices for these dates

Tonight
5 Nov - 6 Nov
Tomorrow
6 Nov - 7 Nov
This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 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.

1. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is Rp2.306.320
Rp2.576.178 total
includes taxes & fees
20 Nov - 21 Nov
The Yankee Inn
An indoor swimming pool with clear blue water, surrounded by windows with a view of trees.

2. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (687 reviews)
  • cleanliness
    Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness centre.
The price is Rp2.281.078
Rp2.547.965 total
includes taxes & fees
6 Dec - 7 Dec
Courtyard by Marriott Lenox Berkshires
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

3. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is Rp2.156.178
Rp2.408.451 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield
Pool

4. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is Rp1.991.244
Rp2.224.219 total
includes taxes & fees
18 Nov - 19 Nov
Hampton Inn & Suites Berkshires-Lenox
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,256 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is Rp1.393.871
Rp1.962.648 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (257 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is Rp1.797.840
Rp2.008.187 total
includes taxes & fees
4 Dec - 5 Dec
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.

7. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (935 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is Rp1.434.640
Rp1.602.494 total
includes taxes & fees
18 Nov - 19 Nov
Howard Johnson by Wyndham Lenox
Outdoor pool

8. Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (527 reviews)
  • cleanliness
    Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
The price is Rp1.241.962
Rp1.391.238 total
includes taxes & fees
18 Nov - 19 Nov
Berkshire Travel Lodge
A large indoor swimming pool with clear blue water, surrounded by white lounge chairs and a few potted plants.

9. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (51 reviews)
  • cleanliness
    Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
The price is Rp2.452.680
Rp2.739.643 total
includes taxes & fees
12 Nov - 13 Nov
Element by Marriott Lenox Berkshires
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

10. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,830 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is Rp1.459.011
Rp1.828.929 total
includes taxes & fees
3 Dec - 4 Dec
Vacation Village in the Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Canaan

Breakfast included
4 stars

Top Canaan Hotel Reviews

A swimming pool with a surrounding deck, a stone wall, and a building in the background.
The Yankee Inn

The Yankee Inn

The Yankee Inn
Lenox

10/10 Excellent

Excellent room. All very clean.
United Kingdom
Martin
Reviewed October 15, 2025
The Yankee Inn

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.