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Find Family Hotels in Canaan, NY

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Check availability on Canaan Family Hotels

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

Top Canaan Family Hotels

Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Cribs/infant beds provided
  • Indoor pool
8.0 out of 10, Very Good, (965)
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 NT$2,614
NT$2,920 total
includes taxes & fees
Dec 22 - Dec 23
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
  • Cribs/infant beds
8.6 out of 10, Excellent, (1001)
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 NT$2,937
NT$3,281 total
includes taxes & fees
Nov 30 - Dec 1
Best Western Plus Berkshire Hills Inn & Suites
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Indoor pool
9.2 out of 10, Wonderful, (1007)
Splash into family fun at this hotel with dual pools, kid-friendly supervised swimming, and microwaves for quick snacks. Just a 3-minute drive from Bousquet Ski Area, the property combines mountain scenery with cozy rooms featuring cable TV and essential comforts.
The price is NT$2,019
NT$2,256 total
includes taxes & fees
Dec 7 - Dec 8
The Yankee, Trademark Collection by Wyndham
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
Great Barrington
  • Cribs/infant beds provided
7.6 out of 10, Good, (560)
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 NT$2,357
NT$2,633 total
includes taxes & fees
Nov 25 - Nov 26
Travelodge by Wyndham Great Barrington Berkshires
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.8 out of 10, Exceptional, (11)
The price is NT$4,116
NT$4,598 total
includes taxes & fees
Dec 11 - Dec 12
Element Lenox Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
  • Cribs/infant beds provided
9.0 out of 10, Wonderful, (1003)
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 NT$3,339
NT$3,729 total
includes taxes & fees
Dec 14 - Dec 15
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
  • Cribs/infant beds provided
  • Indoor pool
9.4 out of 10, Exceptional, (60)
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 NT$3,117
NT$3,482 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
  • Cribs/infant beds provided
  • Indoor pool
9.2 out of 10, Wonderful, (587)
Splash into adventure at this welcoming retreat, where the indoor swimming pool provides year-round fun while Netflix and premium channels entertain after outdoor explorations. Located just 6 minutes from Bousquet Ski Area, families enjoy complimentary cribs and parking.
The price is NT$3,991
NT$4,458 total
includes taxes & fees
Nov 30 - Dec 1
Courtyard by Marriott Lenox Berkshires
Skiing
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
  • Outdoor pool
8.2 out of 10, Very Good, (986)
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 NT$4,682
NT$5,230 total
includes taxes & fees
Nov 24 - Nov 25
Jiminy Peak Mountain Resort
Property amenity
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
  • Cribs/infant beds provided
  • Arcade/game room
9.4 out of 10, Exceptional, (755)
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 NT$4,745
NT$5,300 total
includes taxes & fees
Nov 30 - Dec 1
Fairfield Inn & Suites by Marriott Great Barrington Lenox/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 Canaan Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Great checking. Great staff, great room."
Ronald 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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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 Lenox Library and Shakespeare and Company.