The Best Hotels with a Pool in Canaan, NY from ₩106,197 in 2025

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Top Canaan Hotels with a Pool

Our top choices for Canaan hotels with a pool

"I was pleasantly surprised to find this gem in the middle of town. Relatively inexpensive for the area. Clean rooms and property. Nice staff. Beautiful pool. Would definitely recommend "

₩174,545 total

includes taxes & fees

Sep 8 - Sep 9

"Amazing place to stay. Can’t wait to go again. "

₩149,532 total

includes taxes & fees

Sep 7 - Sep 8

"Perfect place for a relaxing getaway! We loved everything! "

₩151,455 total

includes taxes & fees

Sep 1 - Sep 2

"My stay was perfect. I can't wait to stay there again. "

₩122,087 total

includes taxes & fees

Sep 1 - Sep 2

1 bedroom, desk, iron/ironing board, free WiFi

"This is a very convenient motel -- it is easy to get to, has a nice pool, quiet area, comfortable room, "

₩132,895 total

includes taxes & fees

Aug 26 - Aug 27

"Brand new hotel. Really nice staff. Great location to Tanglewood and great rates. "

₩208,870 total

includes taxes & fees

Sep 1 - Sep 2

"Consistently a clean room with welcoming staff."

₩168,454 total

includes taxes & fees

Sep 1 - Sep 2

"New hotel very nice"

₩234,909 total

includes taxes & fees

Sep 1 - Sep 2

Top Canaan Hotel Reviews

The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Great option a little further away from Lenox! Clean and great service. "

Vacation Village in the Berkshires

10/10 Excellent

"Staff was pleasant and helpful, apartment was spacious and clean. For about the same price as a hotel room, we had a 1 bedroom apartment with a ptl. kitchen (full size fridge with freezer, microwave, 2 burner cooktop, large sink) and resort amenities (indoor, outdoor and kid's pool and a hot tub) and activities. "