Find Hotels with a Pool in Canaan, CT

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Check availability on Canaan Hotels with a Pool

Our top choices for Canaan hotels with a pool

Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18 reviews)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ₩311,362
₩397,009 total
includes taxes & fees
Jan 25 - Jan 26
Prospect Berkshires
Indoor pool
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (719 reviews)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is ₩157,150
₩175,537 total
includes taxes & fees
Jan 22 - Jan 23
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548 reviews)
"Perfect for pets "
United States
Maria
The price is ₩161,556
₩180,459 total
includes taxes & fees
Jan 20 - Jan 21
The Little Lion
2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (818 reviews)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is ₩156,996
₩204,251 total
includes taxes & fees
Jan 15 - Jan 16
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Seasonal outdoor pool
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (275 reviews)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is ₩263,042
₩302,498 total
includes taxes & fees
Jan 15 - Jan 16
Interlaken Inn & Resort
Indoor pool
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (761 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is ₩198,273
₩221,470 total
includes taxes & fees
Jan 29 - Jan 30
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Property grounds
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,001 reviews)
"Old time charm and hot tub under the stars"
United States
Lori
The price is ₩223,119
₩315,248 total
includes taxes & fees
Jan 28 - Jan 29
The Red Lion Inn
Seasonal outdoor pool
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (166 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is ₩241,379
₩277,586 total
includes taxes & fees
Jan 19 - Jan 20
Blackberry River Inn
Seasonal outdoor pool
Sunset Inn

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is ₩132,182
₩147,648 total
includes taxes & fees
Jan 15 - Jan 16
Sunset Inn
Seasonal outdoor pool
Little Cat Lodge

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (66 reviews)
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "
United States
kim
Little Cat 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.
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Top Canaan Hotel Reviews

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"The motel is located not far from what you need. We went to the Lee Outlets and it was 18 minutes. The condition was a little dated but clean and the bed was comfortable and thats very important for us ! The woman who welcomed us was very kind and friendly ! Besides it being outdated i love being able to park right outside your door instead of having to bring all of your things inside through the lobby and up an elevator or stairs !I would stay again 😁 I recommend staying if you dont mind it not being fancy ,the price was reasonable also. The main thing i like is that it is CLEAN ✔️"
Shannon 1-night trip
Posted 8 days ago
Monument Mountain Motel

Frequently asked questions

What are some accommodations with pools in Canaan?
The Red Lion Inn: Features complimentary wireless internet access, a pool, and kitchens. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Offers 3 restaurants, an outdoor pool, and spa services. The Litchfield Inn: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Days Inn by Wyndham Torrington: Features buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express Hotel & Suites Great Barrington by IHG: Offers a sauna, an outdoor pool, and spa services.
What is there to see and do in Canaan?
Spend some time experiencing the great outdoors at Housatonic River and Eddy Field. During your stay, check out sights such as Campbell Falls State Park, Edith Scoville Memorial Sanctuary, and Lawrence Field.
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.