Find Hotels with a Pool in Canaan, CT

Start date: Check-in selected.
To Date
End date: Check-out

    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 Hotels with a Pool

Top Canaan Hotels with a Pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (674)
"Great place to have a girls night for old friends when one of us is back in town for a night. Very convenient place well kept. "
The price is ₩147,214
₩164,432 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Prospect Berkshires
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers

Prospect Berkshires

3.0 star property
9.0 out of 10, Wonderful, (7)
"Gorgeous thoughtfully designed cabins with so many amenities/activities. Cliff house restaurant was delicious. Perfect getaway. "
The price is ₩370,887
₩462,083 total
includes taxes & fees
Nov 2 - Nov 3
Prospect Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers

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

3.5 star property
9.0 out of 10, Wonderful, (754)
"The lodging was convenient to all the area attractions."
The price is ₩165,615
₩204,906 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Blackberry River Inn
Seasonal outdoor pool

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (143)
"Loved everything especially Lucas and Joe💟☮️"
The price is ₩234,444
₩269,611 total
includes taxes & fees
Oct 14 - Oct 15
Blackberry River Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Indoor pool

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (743)
"The property is very nice and the staff was extremely friendly and helpful."
The price is ₩203,988
₩227,855 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Cornwall Inn and Lodge
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

Cornwall Inn and Lodge

3.0 star property
9.2 out of 10, Wonderful, (148)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
The price is ₩283,872
₩326,453 total
includes taxes & fees
Nov 1 - Nov 2
Cornwall Inn and Lodge
Little Cat Lodge
Seasonal outdoor pool

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (60)
"Atmosphere, service and food was excellent. Definitely going back!"
The price is ₩242,646
₩271,764 total
includes taxes & fees
Oct 14 - Oct 15
Little Cat Lodge
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (407)
"The staff is a one man operation,Which he is a very nice man,does a good job keeping up with the cleaning.Location is great walking distance to the town and plenty of restaurants."
The price is ₩128,384
₩143,405 total
includes taxes & fees
Nov 3 - Nov 4
Sunset Inn
Interlaken Inn & Resort
Seasonal outdoor pool

Interlaken Inn & Resort

3.5 star property
8.2 out of 10, Very Good, (265)
"The staff is courteous and accommodating especially the restaurant staff."
The price is ₩319,676
₩367,627 total
includes taxes & fees
Oct 26 - Oct 27
Interlaken Inn & Resort
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (107)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
The price is ₩441,456
₩534,045 total
includes taxes & fees
Oct 27 - Oct 28
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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.
View all properties

Top Canaan Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent
"I would say 4.7 out of five stars. Clean friendly, very comfortable bed nice breakfast. My only complaint would be the toilet paper could be a better quality…"
Kenneth 2-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Frequently asked questions

What are some accommodations with pools in Canaan?
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Red Lion Inn: Offers 3 restaurants, an outdoor pool, and spa services. Quality Inn: Offers buffet, an indoor pool, and complimentary wired internet access. The Litchfield Inn: Features full, an indoor pool, and complimentary wired internet access. Holiday Inn Express Hotel & Suites Great Barrington by IHG: Offers cooked-to-order, a seasonal outdoor pool, and free self parking.
What is there to see and do in Canaan?
Spend some time experiencing the great outdoors at Housatonic River and Beckley Furnace Industrial Park. During your stay, check out sights such as Campbell Falls State Park, North Canaan Town Hall, and Edith Scoville Memorial Sanctuary.
When is the best time to book a hotel with a pool in Canaan?
Taking into account the local weather in Canaan is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.