Find Hotels with a Pool in Canaan, CT

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Check availability on Canaan Hotels with a Pool

Tonight
Dec 4 - Dec 5
Tomorrow
Dec 5 - Dec 6
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Top Canaan Hotels with a Pool

Indoor pool
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, (702)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is ￥16,594
￥18,535 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is ￥18,687
￥27,834 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Red Lion Inn
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

3.5 star property
South Lee
9.0 out of 10, Wonderful, (794)
"Place was great!"
United States
Benjamin
The price is ￥16,516
￥21,162 total
includes taxes & fees
Dec 8 - Dec 9
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (410)
"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 ￥13,538
￥15,121 total
includes taxes & fees
Dec 5 - Dec 6
Sunset Inn
Seasonal outdoor pool
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (162)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is ￥25,488
￥29,311 total
includes taxes & fees
Dec 8 - Dec 9
Blackberry River Inn
Outdoor pool
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is ￥40,755
￥47,801 total
includes taxes & fees
Dec 21 - Dec 22
The Inn at Stockbridge
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

3.0 star property
Great Barrington
8.6 out of 10, Excellent, (547)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is ￥17,135
￥19,140 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Little Lion
Outdoor pool, sun loungers
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Seasonal outdoor pool
Little Cat Lodge

Little Cat Lodge

2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (66)
"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
Indoor pool
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, (757)
"Clean room, very courteous staff "
United States
Thomas
The price is ￥23,417
￥26,157 total
includes taxes & fees
Dec 9 - Dec 10
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 rm was perfect. Bed, table and chairs, tv, and good size bath. Was here 3 days to see family. Very friendly,comfortable bed and very clean. Walking distance to supermarket and dining and bowling. I will rent again."
Laura 3-night trip
Posted 6 days ago
Monument Mountain Motel

Frequently asked questions

What are some accommodations with pools in Canaan?
The Red Lion Inn: Features 3 restaurants, an outdoor pool, and spa services. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Quality Inn: Features buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express Hotel & Suites Great Barrington by IHG: Provides a full-service spa, a seasonal outdoor pool, and 3 outdoor tennis courts. The Litchfield Inn: Features full, an indoor pool, and complimentary wired internet access.
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, 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.