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

Hotels with Swimming Pools in Canaan

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Check availability on Canaan Hotels with Swimming Pools

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

Our top choices for Canaan hotels with a pool

1. 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
1 Sept - 2 Sept
Berkshire Travel Lodge

2. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
S$226
includes taxes & fees
14 Sept - 15 Sept
The Yankee Inn

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
S$164
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.
S$195
includes taxes & fees
14 Sept - 15 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.
S$113
includes taxes & fees
1 Sept - 2 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.
S$181
includes taxes & fees
14 Sept - 15 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.
S$170
includes taxes & fees
16 Sept - 17 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.
S$211
includes taxes & fees
13 Sept - 14 Sept
Hilton Garden Inn Lenox Pittsfield

9. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
S$289
includes taxes & fees
14 Sept - 15 Sept
The Red Lion Inn

10. Berkshire Inn

Berkshire Inn
Pittsfield
  • Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
S$128
includes taxes & fees
27 Aug - 28 Aug
Berkshire 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

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 5 hours ago
Howard Johnson by Wyndham Lenox
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Maintenance problems in room. Property made up for it."
Steve 1-night trip
Posted 14 hours ago
The Red Lion Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"This is a great resort with large, clean, well equipped rooms. My only gripe is the location is quite remote and you have to drive 10 minutes for food."
Benjamin 7-night trip
Posted 15 hours ago
Vacation Village in the Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Lovely location on Laurel lake. Our balcony was directly over looking the lake. A wonderful spot for morning coffee and a book. Dogs are welcome! Well behaved, of course. A short drive to Lenox, Tanglewood and Stockbridge. Always coming back!"
Megan 2-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"…."
Tiago 3-night trip
Posted 2 days ago
Jiminy Peak Mountain Resort
The Yankee Inn

The Yankee Inn

8/10 Good
"The stay was very good however the rooms are dated though well maintained. I felt the price was very high for the accommodations. I had expected more for the price ($350) but it was their peak season and they need to price accordingly. Certainly this Inn did not offer the feel or quality level of even a Holiday Inn or Hampton Inn. That being said it was very clean, the staff was very friendly and the breakfast was good."
Gary 1-night trip
Posted 2 days ago
The Yankee Inn
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 3 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.

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