Hotels with Swimming Pools in Canaan

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 Swimming Pools

Top Hotels with Swimming Pools in Canaan

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 S$149
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Prospect Berkshires
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, pool 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 S$467
includes taxes & fees
2 Nov - 3 Nov
Prospect Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
2 indoor pools, 2 outdoor pools, pool umbrellas, pool loungers

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

3.5 star property
9.0 out of 10, Wonderful, (752)
"The lodging was convenient to all the area attractions."
The price is S$186
includes taxes & fees
2 Nov - 3 Nov
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, (142)
"Loved everything especially Lucas and Joe💟☮️"
The price is S$245
includes taxes & fees
14 Oct - 15 Oct
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 S$207
includes taxes & fees
2 Nov - 3 Nov
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 S$297
includes taxes & fees
1 Nov - 2 Nov
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!"
Little Cat Lodge
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (406)
"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 S$149
includes taxes & fees
16 Oct - 17 Oct
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 S$334
includes taxes & fees
26 Oct - 27 Oct
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, pool loungers

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

4.5 star property
9.2 out of 10, Wonderful, (106)
"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 S$486
includes taxes & fees
27 Oct - 28 Oct
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Lovely historic hotel that we enjoyed but also knew going in not to expect modern…yes the floors creak and doors and windows dont fit snuggly. We loved it for all those reasns! Staff is wonderful! Enjoy the front porch while you are there!"
Connie 1-night trip
Posted 7 days ago
The Red Lion Inn

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodation options with pools in Canaan?
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Features 2 indoor swimming pools, 2 outdoor swimming 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 high-speed (wired) Internet access. The Litchfield Inn: Features full, an indoor pool and complimentary high-speed (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 Edith Scoville Memorial Sanctuary. During your stay, visit sights such as Campbell Falls State Park, North Canaan Town Hall and Lawrence Field.
When is the best time to book a hotel with a pool in Canaan?
Taking the local weather in Canaan into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Canaan are January, March, February and November, with each month seeing an average of 18 cm of snowfall.