Hotels with Swimming Pool in North Canaan, Connecticut

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Check availability on North Canaan Hotels with Swimming Pool

Our top choices for North Canaan hotels with a pool

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 P9,754
P11,217 total
includes taxes & fees
Jan 19 - Jan 20
Blackberry River Inn
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, (722 reviews)
"Always love staying here. The staff is fantastic, amenities are great, and the breakfast is just lovely. Will be returning soon!"
United States
Domenic
The price is P6,350
P7,093 total
includes taxes & fees
Jan 21 - Jan 22
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (822 reviews)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is P6,677
P8,618 total
includes taxes & fees
Jan 21 - Jan 22
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (549 reviews)
"Perfect for pets "
United States
Maria
The price is P6,528
P7,292 total
includes taxes & fees
Jan 19 - Jan 20
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 P8,902
P12,595 total
includes taxes & fees
Jan 19 - Jan 20
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 P5,341
P5,966 total
includes taxes & fees
Jan 19 - Jan 20
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, (763 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is P8,012
P8,949 total
includes taxes & fees
Jan 29 - Jan 30
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 P12,558
P14,442 total
includes taxes & fees
Jan 19 - Jan 20
Cornwall Inn and Lodge
Seasonal outdoor pool

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (276 reviews)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is P10,629
P12,223 total
includes taxes & fees
Jan 21 - Jan 22
Interlaken Inn & Resort
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)
"It was clean and environment is relaxing."
United States
KEYA
The price is P10,208
P13,391 total
includes taxes & fees
Jan 27 - Jan 28
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 North Canaan Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"everything"
Brian 2-night trip
Posted 6 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Frequently asked questions

What are some accommodations with pools in North Canaan?
Blackberry River Inn: Features cooked-to-order, a seasonal outdoor pool, and free self parking. Locust Tree Bed and Breakfast LLC: Provides complimentary wireless internet access, a pool, and kitchens. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Red Lion Inn: Offers 3 restaurants, an outdoor pool, and spa services. The Litchfield Inn: Offers buffet, an indoor pool, and complimentary wired internet access.
What is there to see and do in North Canaan?
Spend some time experiencing the great outdoors at Housatonic River. During your stay, check out sights such as Land of Nod Vineyard and Winery, Campbell Falls State Park, and Lawrence Field.
When is the best time to book a hotel with a pool in North Canaan?
Taking into account the local weather in North 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 North Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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