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

Canaan Hotel with Pool

  • 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 Hotel with Pool

Tonight
20 Aug - 21 Aug
Tomorrow
21 Aug - 22 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Canaan hotels with a pool

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
HK$1,239
HK$1,384 total
includes taxes & fees
14 Sept - 15 Sept
The Yankee Inn

2. 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.
HK$529
HK$593 total
includes taxes & fees
25 Aug - 26 Aug
Berkshire Travel Lodge

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
HK$742
HK$1,004 total
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge

4. 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.
HK$1,074
HK$1,199 total
includes taxes & fees
20 Sept - 21 Sept
Hampton Inn & Suites Berkshires-Lenox

5. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
HK$619
HK$692 total
includes taxes & fees
3 Sept - 4 Sept
Howard Johnson by Wyndham Lenox

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.
HK$996
HK$1,112 total
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

7. 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.
HK$933
HK$1,042 total
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG

8. 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.
HK$1,147
HK$1,281 total
includes taxes & fees
13 Sept - 14 Sept
Hilton Garden Inn Lenox Pittsfield

9. Berkshire Inn

Berkshire Inn
Pittsfield
  • Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
HK$706
HK$788 total
includes taxes & fees
24 Aug - 25 Aug
Berkshire Inn

10. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
HK$1,304
HK$1,846 total
includes taxes & fees
14 Sept - 15 Sept
The Red Lion Inn
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
"What a wonderful stay! It was an impromptu overnight to the Berkshires and I’m so glad we chose to stay here. Our room was beautiful and clean, with a lovely view of the pond area out back from the balcony. Great bathroom and shower, very clean. Breakfast was yummy with a nice selection. The pools and hot tub were the BEST part. I absolutely will be back because one night was certainly not enough."
Kelly 1-night trip
Posted 11 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"We only stayed a night but the rooms were clean enough and the staff was extremely kind. Would stay here again."
Sisile 1-night trip
Posted 13 hours ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Perfect."
gordon 1-night trip
Posted 20 hours ago
The Red Lion Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"The motel is in a great location. You could walk to everything. The room was clean and comfortable although the air conditioning in the room didn't work very well. The fan ran but it didn't cool the room."
Jen 1-night trip
Posted 1 day ago
Howard Johnson by Wyndham Lenox
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"…."
Tiago 3-night trip
Posted 3 days ago
Jiminy Peak Mountain Resort
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"0nly 1 of 3 elevators was working. It was a 11 story building, and there was a lot of waiting. My room was wonderful, very clean, and with a fabulous view."
Linda 1-night trip
Posted 4 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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. The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool and buffet. Berkshire Mountain Lodge: Provides free self parking, an indoor pool and complimentary wireless Internet access. FairBridge Inn Express: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Berkshires Untold: 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