Hotels with Swimming Pool in Canaan, Connecticut

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Check availability on Canaan Hotels with Swimming Pool

Tonight
Nov 23 - Nov 24
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Nov 24 - Nov 25
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Top Canaan Hotels with Swimming 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
  • Indoor pool
8.8 out of 10, Excellent, (697)
Splash into the warm, pristine indoor pool after exploring nearby hiking trails or skiing at Butternut. Modern rooms with premium bedding await, while a complimentary breakfast buffet energizes adventures in Great Barrington's vibrant surroundings.
The price is P6,296
P7,033 total
includes taxes & fees
Nov 30 - Dec 1
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
  • Near the beach
7.6 out of 10, Good, (410)
Mountain recreation surrounds this quiet getaway featuring a refreshing seasonal pool open from August. After swimming, guests appreciate clean, comfortable rooms with mini fridges before exploring nearby skiing and hiking trails.
The price is P5,296
P5,916 total
includes taxes & fees
Dec 2 - Dec 3
Sunset 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
  • 2 outdoor pools
  • 2 indoor pools
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (789)
Swimming enthusiasts rejoice at this four-pool paradise nestled in the Berkshires. Families appreciate the well-maintained waters complemented by sun loungers, umbrellas, and refreshing poolside drinks, creating memorable mountain getaways year-round.
The price is P6,267
P7,822 total
includes taxes & fees
Nov 30 - Dec 1
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
  • Outdoor pool
  • Pool loungers
8.8 out of 10, Excellent, (1002)
Sparkling waters invite refreshment at the outdoor pool, complemented by a rejuvenating hot tub that remains open year-round. Beyond aquatic pleasures, this historic hotel enchants with excellent dining, tasteful accommodations, and friendly service.
The price is P8,768
P12,423 total
includes taxes & fees
Dec 15 - Dec 16
The Red Lion 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
  • Indoor pool
9.4 out of 10, Exceptional, (755)
Splashing fun awaits in the pristine indoor swimming pool, complemented by a relaxing hot tub for post-adventure recovery. Families particularly appreciate these well-maintained aquatic amenities alongside the hotel's spotlessly clean rooms and friendly staff.
The price is P8,885
P9,925 total
includes taxes & fees
Nov 30 - Dec 1
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
  • Outdoor pool
  • Pool loungers
9.6 out of 10, Exceptional, (14)
Mountain adventures begin at the outdoor pool, complete with sun loungers and umbrellas for post-hike relaxation. Sauna sessions, complimentary bicycles, and nearby hiking trails complement the experience at this scenic Berkshire retreat.
The price is P15,299
P19,061 total
includes taxes & fees
Nov 24 - Nov 25
Prospect Berkshires
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

3.0 star property
Great Barrington
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • Extra beds/cribs
8.6 out of 10, Excellent, (544)
Aquatic adventures beckon with access to a nearby outdoor pool, complementing garden strolls at this cozy Berkshire motel. Nestled close to Norman Rockwell Museum and Ski Butternut, guests praise the helpful staff and comfortable accommodations.
The price is P7,591
P8,479 total
includes taxes & fees
Nov 24 - Nov 25
The Little Lion
Seasonal outdoor pool
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Business services
  • Housekeeping
9.4 out of 10, Exceptional, (159)
Dive into summer bliss at the seasonal outdoor pool, open June through September, after enjoying the complimentary cooked-to-order breakfast. Surrounded by quiet countryside, this bed & breakfast offers fireplace warmth, picnic areas, and attentive service from helpful staff.
The price is P9,671
P11,122 total
includes taxes & fees
Nov 25 - Nov 26
Blackberry River Inn
Seasonal outdoor pool
Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 star property
Lakeville
  • Full-service spa
8.2 out of 10, Very Good, (270)
Seasonal swimming awaits from May through September at this recreational haven featuring three outdoor tennis courts and hiking trails. Massage treatments, bike rentals, and an arcade room complement the active outdoor lifestyle of this countryside retreat.
The price is P13,187
P15,165 total
includes taxes & fees
Nov 24 - Nov 25
Interlaken Inn & Resort
Seasonal outdoor pool
Little Cat Lodge

Little Cat Lodge

2.0 star property
Copake Falls
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
9.4 out of 10, Exceptional, (64)
Seasonal outdoor swimming provides mountain refreshment after exploring nearby hiking trails or skiing adventures. Relaxation continues in the sauna, while evenings bring gatherings around the firepit under starry skies after a delicious continental breakfast.
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

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

10/10 Excellent
"Very nice people at the desk, room was very nice"
Joseph 1-night trip
Posted 2 days ago
Travelodge by Wyndham Great Barrington Berkshires

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. Holiday Inn Express Hotel & Suites Great Barrington by IHG: Provides buffet, an indoor pool, and complimentary wired internet access. Americas Best Value Inn Torrington CT: Features full, an indoor pool, and complimentary wired internet access. Days Inn by Wyndham Torrington: Features a full-service spa, a seasonal outdoor pool, and 3 outdoor tennis courts.
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 North Canaan Town Hall, Campbell Falls State Park, 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.