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

Search Hotels with Pool in Canaan

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Check availability on Canaan Hotels with Pool

Tonight
30 Aug - 31 Aug
Tomorrow
31 Aug - 1 Sep
Next weekend
4 Sep - 6 Sep
In two weeks
11 Sep - 13 Sep

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.
3.963.856 ₫
4.427.523 ₫ total
includes taxes & fees
27 Sept - 28 Sept
The Yankee Inn

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
2.466.879 ₫
3.338.086 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge

3. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
2.060.162 ₫
2.301.200 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Howard Johnson by Wyndham Lenox

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.
3.237.679 ₫
3.616.506 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Hampton Inn & Suites Berkshires-Lenox

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.
3.077.204 ₫
3.437.341 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

6. 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.
3.077.204 ₫
3.437.341 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG

7. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
4.107.807 ₫
5.883.976 ₫ total
includes taxes & fees
29 Sept - 30 Sept
The Red Lion Inn

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.
1.760.004 ₫
1.971.236 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Berkshire Travel Lodge

9. 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.
3.862.673 ₫
4.314.607 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Hilton Garden Inn Lenox Pittsfield

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.
2.242.447 ₫
2.504.812 ₫ total
includes taxes & fees
31 Aug - 1 Sept
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

The Yankee Inn

The Yankee Inn

8/10 Good
"Independent option convenient to Tanglewood. Spacious room and facility. Breakfast included but needs better coffee and some other tweaks."
Francis 1-night trip
Posted 3 hours ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Friendly and professional staff. Check in quick and easy. Will definitely stay again"
abdoul kader 1-night trip
Posted 21 hours ago
Vacation Village in the Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Location"
patricia 2-night trip
Posted 21 hours ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
Dorothy 1-night trip
Posted 2 days ago
The Red Lion Inn
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"I am not a person who usually writes a review but I loved the place. Room was great. Staff was great. I had never been to an Indian restaurant but everywhere I went people raved about I so we went and it was wonderful. Only a few small issues. The fan in our bathroom room needs attention. Very loud. Something is failing. The wifi was very weak in my room. Kept cutting out. and just one other suggestion. The balcony on the upper level should have privacy screens on the sides. Other wise I would absolutely go back."
JAMES 2-night trip
Posted 3 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

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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