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Top Hillsdale Family-Friendly Hotels

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
  • Cots/infant beds
8.6 out of 10, Excellent, (1003)
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 2.465.442 ₫
2.753.900 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Berkshire Hills Inn & Suites

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
  • Cots/infant beds provided
9.0 out of 10, Wonderful, (1005)
Playtime paradise awaits with free cots, 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 2.801.281 ₫
3.129.031 ₫ total
includes taxes & fees
19 Dec - 20 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.8 out of 10, Exceptional, (11)
The price is 3.454.994 ₫
3.859.228 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Element Lenox Berkshires

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
  • Cots/infant beds provided
  • Indoor pool
9.2 out of 10, Wonderful, (63)
Vacation-ready accommodation feature premium TV channels and complimentary cots for little travellers. Mornings begin with a free breakfast buffet, fuelling adventures to nearby attractions. Spotlessly clean facilities and cheerful staff ensure a relaxing family retreat.
The price is 2.510.805 ₫
2.804.568 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Cots/infant beds provided
  • Indoor pool
8.0 out of 10, Very good, (973)
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 cots and rollaway beds, alongside a restaurant serving delicious meals for hungry explorers.
The price is 2.448.781 ₫
2.735.287 ₫ total
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
  • Cots/infant beds provided
7.6 out of 10, Good, (560)
Family holidays shine at this peaceful Berkshire retreat offering complimentary cots and rollaway beds for little ones. The refreshing pool delights with sunny and shaded areas, while the spotless accommodation and helpful staff ensure carefree comfort for travellers of all ages.
The price is 1.978.050 ₫
2.209.614 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Travelodge by Wyndham Great Barrington Berkshires

Howard Johnson by Wyndham Saugerties

2.0 star property
Saugerties
  • Cots/infant beds provided
  • Indoor pool
7.6 out of 10, Good, (1004)
Families splash in the pristine indoor pool while parents unwind in the rejuvenating sauna after exploring nearby Seamon Park. Thoughtful touches include complimentary cots, spacious rooms with microwaves and refrigerators, and the restaurant's generous portions that satisfy hungry adventurers.
The price is 2.331.462 ₫
2.611.554 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Howard Johnson by Wyndham Saugerties

Spark by Hilton West Coxsackie

2.5 star property
West Coxsackie
  • Cots/infant beds provided
  • Indoor pool
7.6 out of 10, Good, (73)
Brightly remodeled accommodation feature premium TV channels, cots, and rollaway beds for family comfort. Hiking and skiing spots surround the hotel's quiet rural setting. Clean, spacious rooms and friendly staff ensure memorable stays.
The price is 2.299.813 ₫
2.483.797 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Spark by Hilton West Coxsackie

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
  • Cots/infant beds provided
  • 2 outdoor pools
  • Arcade/games room
9.0 out of 10, Wonderful, (790)
The price is 2.807.873 ₫
3.504.448 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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, (65)
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.

Top Hillsdale Hotel Reviews

Frequently asked questions

What's Hillsdale like for family-friendly holidays?
The relaxing destination of Hillsdale is a great choice if you've been considering a holiday with the children. The horse riding, coffee shops and libraries are just a few things that make this an attractive spot for a family holiday. Take to the air and fly into Hudson, NY (HCC-Columbia County), which is located 12.5 mi (20.1 km) from the city centre.
When's the best time to book a family-friendly holiday in Hillsdale?
The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillsdale are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What's there to see and do with your family in Hillsdale?
Catamount Ski Area, Community Library and Mahaiwe Performing Arts Center are interesting attractions that you and your family will enjoy exploring while you are staying in Hillsdale. Make sure that you have lots of time for activities such as Ski Butternut and Lake Taghkanic State Park.