Hotels with Pool & Resorts in Canaan from NZ$173

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Check availability on Canaan Hotels with Pool

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for 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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (714)
"We stay here every year and it never disappoints "
United States
Elizabeth
The price is NZ$189
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, pool loungers
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18)
"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 NZ$523
includes taxes & fees
25 Jan - 26 Jan 2026
Prospect Berkshires
Outdoor pool, pool 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)
"Old time charm and hot tub under the stars"
United States
Lori
The price is NZ$352
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn
Iron/ironing board, free cots/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, (548)
"Perfect for pets "
United States
Maria
The price is NZ$212
includes taxes & fees
1 Jan - 2 Jan 2026
The Little Lion
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, (759)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is NZ$260
includes taxes & fees
27 Jan - 28 Jan 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2 indoor pools, 2 outdoor pools, pool umbrellas, pool 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, (813)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is NZ$266
includes taxes & fees
5 Jan - 6 Jan 2026
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, (274)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is NZ$355
includes taxes & fees
1 Jan - 2 Jan 2026
Interlaken Inn & Resort
Seasonal outdoor pool
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (166)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is NZ$325
includes taxes & fees
5 Jan - 6 Jan 2026
Blackberry River 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
The price is NZ$173
includes taxes & fees
11 Jan - 12 Jan 2026
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)
"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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Very clean. Nice staff"
Rosael 2-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Frequently asked questions

What are some accommodation options 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 swimming pools, 2 outdoor swimming pools and a snack bar/deli. Holiday Inn Express Hotel & Suites Great Barrington by IHG: Provides buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Litchfield Inn: Offers full, an indoor pool and complimentary high-speed (wired) Internet access. Days Inn by Wyndham Torrington: Features 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, visit 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 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.