Photo by Robin/Loving Life

Find Hotels with a Pool in Canaan, NY

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check availability on Canaan Hotels with a Pool

Tonight
22 Jun - 23 Jun
Tomorrow
23 Jun - 24 Jun
Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul

Top Canaan Hotels with a Pool

The Old Inn On The Green
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (84)
"Beautiful room and property. Perfect weekend getaway!"
The price is SAR 1,088
SAR 1,313 total
includes taxes & fees
23 Jun - 24 Jun
The Old Inn On The Green
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is SAR 447
SAR 583 total
includes taxes & fees
29 Jun - 30 Jun
Deluxe Queen Room with 2 Queen Beds
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (381)
"The room was clean and perfect for our stay."
The price is SAR 342
SAR 382 total
includes taxes & fees
7 Jul - 8 Jul
Sunset Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (126)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (659)
"Wonderful property we’ve been coming here for years"
The price is SAR 469
SAR 577 total
includes taxes & fees
23 Jun - 24 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The price is SAR 861
SAR 962 total
includes taxes & fees
13 Jul - 14 Jul
The Ponds at Foxhollow
Holiday Inn Express & Suites Pittsfield - Berkshires
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
The price is SAR 784
SAR 876 total
includes taxes & fees
20 Jul - 21 Jul
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (635)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is SAR 737
SAR 823 total
includes taxes & fees
25 Jun - 26 Jun
Hilton Garden Inn Lenox Pittsfield
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (736)
"Was great loved the jacuzzi tub "
The price is SAR 334
SAR 373 total
includes taxes & fees
23 Jun - 24 Jun
Howard Johnson by Wyndham Lenox
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (492)
"We enjoyed our stay here. It was very quiet, and had everything we needed."
Berkshire Mountain Lodge
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.

Frequently asked questions

What are some hotels with pools in Canaan?
Comfort Inn & Suites East Greenbush - Albany: Features buffet, an indoor pool, and free self parking. Quality Inn: Features a seasonal outdoor pool, an indoor pool, and buffet. Holiday Inn Express Hotel & Suites West Coxsackie by IHG: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. The Yankee, Trademark Collection by Wyndham: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Best Western Plus Berkshire Hills Inn & Suites: Provides a sauna, a seasonal outdoor pool, and free valet parking.
What is there to see and do in Canaan?
The picturesque setting of Queechy Lake showcases the area's natural beauty. During your stay, check out 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 into account the local weather in Canaan can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.