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Find Family Hotels in Canaan, NY

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Check availability on Canaan Family Hotels

Tonight
29 Oct - 30 Oct
Tomorrow
30 Oct - 31 Oct
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Top Canaan Family Hotels

Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
  • Cribs/infant beds
8.6 out of 10, Excellent, (1022)
Family memories await at this thoughtful property, featuring spacious suites with premium TV channels and blackout drapes for restful evenings. Complimentary breakfast fuels adventures before heading to nearby Bousquet Ski Area, just a quick 5-minute drive away.
The price is AED 358
AED 400 total
includes taxes & fees
2 Nov - 3 Nov
Best Western Plus Berkshire Hills Inn & Suites
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
  • Cribs/infant beds provided
  • Indoor pool
8.0 out of 10, Very Good, (929)
Spacious suites accommodate families with comfort, while children splash in the heated indoor pool year-round. Located steps from Berkshire Museum, this hotel offers complimentary cribs and rollaway beds, alongside a restaurant serving delicious meals for hungry explorers.
The price is AED 378
AED 423 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
  • Cribs/infant beds provided
9.0 out of 10, Wonderful, (1000)
Playtime paradise awaits with free cribs, kayaking on the sparkling lake, and motor boating adventures. Children delight in fishing excursions, premium TV entertainment, and beachside fun while parents appreciate the lakefront setting and complimentary breakfast each morning.
The price is AED 390
AED 436 total
includes taxes & fees
4 Nov - 5 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Element Lenox Berkshires
Element Lenox Berkshires
3.0 star property
  • Indoor pool
9.4 out of 10, Exceptional, (6)
The price is AED 496
AED 554 total
includes taxes & fees
6 Nov - 7 Nov
Element Lenox Berkshires
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
  • Cribs/infant beds provided
7.6 out of 10, Good, (556)
Family vacations shine at this peaceful Berkshire retreat offering complimentary cribs and rollaway beds for little ones. The refreshing pool delights with sunny and shaded areas, while the spotless accommodations and helpful staff ensure carefree comfort for travelers of all ages.
The price is AED 275
AED 308 total
includes taxes & fees
2 Nov - 3 Nov
Travelodge by Wyndham Great Barrington Berkshires
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
  • Cribs/infant beds provided
  • Indoor pool
9.4 out of 10, Exceptional, (55)
Vacation-ready accommodations feature premium TV channels and complimentary cribs for little travelers. Mornings begin with a free breakfast buffet, fueling adventures to nearby attractions. Spotlessly clean facilities and cheerful staff ensure a relaxing family retreat.
The price is AED 465
AED 520 total
includes taxes & fees
4 Nov - 5 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Property amenity
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
  • Cribs/infant beds provided
  • Arcade/game room
9.4 out of 10, Exceptional, (747)
Vibrant game room captivates young adventurers while parents unwind in the soundproof accommodations or hot tub. After complimentary breakfast, families explore nearby skiing or Housatonic River Walk, returning to swim sessions in the pristine indoor pool.
The price is AED 525
AED 587 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Skiing
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3.0 star property
  • Outdoor pool
8.2 out of 10, Very Good, (984)
Mountain adventures captivate young travelers at this ski-in/ski-out resort with an outdoor pool, tennis courts, and fully equipped kitchens. Families appreciate the quiet atmosphere, friendly staff, and variety of seasonal activities from skiing to biking.
The price is AED 547
AED 611 total
includes taxes & fees
30 Oct - 31 Oct
Jiminy Peak Mountain Resort
Lobby
Comfort Inn & Suites East Greenbush - Albany
Comfort Inn & Suites East Greenbush - Albany
2.5 star property
  • Indoor pool
8.4 out of 10, Very Good, (1001)
The price is AED 387
AED 430 total
includes taxes & fees
14 Nov - 15 Nov
Comfort Inn & Suites East Greenbush - Albany
Seasonal outdoor pool
Little Cat Lodge
Little Cat Lodge
2.0 star property
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
9.4 out of 10, Exceptional, (63)
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Good location; reasonable price; very clean and quiet - would definitely return"
Steven 2-night trip
Posted 1 day ago
Vacation Village in the Berkshires

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Frequently asked questions

What's Canaan like for family-friendly vacations?
If you've been thinking about a trip with your kids, the budget-friendly destination of Canaan is a good choice. The museums, local tours, and coffee shops are just some of the things that make this an attractive family vacation spot. Take to the air and fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest airport, or Hudson, NY (HCC-Columbia County), which is located 15.8 mi (25.4 km) from the city center.
When's the best time to book a family-friendly vacation in Canaan?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's there to see and do with your family in Canaan?
While you are visiting Canaan, you might want to round up the kiddos and make time to see interesting attractions such as Tanglewood Music Center and Bousquet Ski Area. Make sure you have lots of time for activities like Shakespeare and Company and Ventfort Hall Mansion and Gilded Age Museum.