Find Hotels with a Pool in Canaan, CT

  • 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 a Pool

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
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (720 reviews)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is ₩156,791
₩175,136 total
includes taxes & fees
Jan 22 - Jan 23
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers

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 ₩252,858
₩331,705 total
includes taxes & fees
Jan 27 - Jan 28
Prospect Berkshires
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, (818 reviews)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is ₩164,851
₩212,786 total
includes taxes & fees
Jan 20 - Jan 21
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Seasonal outdoor pool

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 ₩262,442
₩301,816 total
includes taxes & fees
Jan 23 - Jan 24
Interlaken Inn & Resort
Exterior

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 ₩161,187
₩180,046 total
includes taxes & fees
Jan 21 - Jan 22
The Little Lion
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"Old time charm and hot tub under the stars"
United States
Lori
The price is ₩227,128
₩319,181 total
includes taxes & fees
Jan 26 - Jan 27
The Red Lion Inn
Seasonal outdoor pool

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 ₩131,881
₩147,311 total
includes taxes & fees
Jan 17 - Jan 18
Sunset Inn
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, (761 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is ₩197,821
₩220,966 total
includes taxes & fees
Jan 29 - Jan 30
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Seasonal outdoor pool

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 ₩240,829
₩276,953 total
includes taxes & fees
Jan 20 - Jan 21
Blackberry River Inn
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (155 reviews)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is ₩310,066
₩356,576 total
includes taxes & fees
Jan 17 - Jan 18
Cornwall Inn and 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.
View all properties

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 11 days ago
Monument Mountain Motel

Frequently asked questions

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