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Find Hotels with an Outdoor Pool in Canaan, NY

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Our top choices for Canaan hotels with an outdoor pool

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
$75 nightly
The price is $84
Dec 24 - Dec 25
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Courtyard
The Springs Motel

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (88)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
$101 nightly
The price is $111
Dec 14 - Dec 15
Total with taxes and fees
The Springs Motel
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
$79 nightly
The price is $89
Dec 14 - Dec 15
Total with taxes and fees
Berkshire Inn
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Dec 14 - Dec 15
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion

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
$110 nightly
The price is $123
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Little Lion
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
$180 nightly
The price is $202
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Red Lion Inn
Seasonal outdoor pool
Sunset Inn

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
$86 nightly
The price is $97
Dec 30 - Dec 31
Total with taxes and fees
Sunset Inn
Property amenity
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, (802)
"Place was great!"
United States
Benjamin
$120 nightly
The price is $134
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2170)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
$126 nightly
The price is $141
Dec 14 - Dec 15
Total with taxes and fees
Vacation Village in the Berkshires
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"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
$203 nightly
The price is $227
Jan 4 - Jan 5, 2026
Total with taxes and fees
Prospect 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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"My husband and I needed a night away between the holidaze and it was perfect! Cozy, clean and warm fireplace to nurture us during a cold snap! Shelly went above and beyond to ensure that we were comfortable and in the quietest part of the hotel. We are booking our family members there"
Sara 1-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

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