A rural landscape with snow-covered fields, a winding road, and scattered trees.

Hillsdale Hotel Guide - Family Friendly Hotels in Hillsdale, New York

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Our top choices for Hillsdale family-friendly hotels

Exterior

Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 reviews)
The price is €570
includes taxes & fees
9 Aug - 10 Aug
Gorgeous Mountain Views Retreat: Family & Nature
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,005 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
The price is €117
includes taxes & fees
14 Jul - 15 Jul
Best Western Plus Berkshire Hills Inn & Suites
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (127 reviews)
  • cleanliness
    Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Centre.
The price is €154
includes taxes & fees
16 Jul - 17 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Free daily continental breakfast

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
2.5 star property
West Coxsackie
8.0 out of 10, Very good, (148 reviews)
  • cleanliness
    Family-friendly fun for all ages at this hotel—explore hiking trails, enjoy free breakfast, or workout in the 24-hour gym.
The price is €106
includes taxes & fees
26 Jul - 27 Jul
Spark by Hilton West Coxsackie
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.6 out of 10, Excellent, (31 reviews)
The price is €248
includes taxes & fees
13 Jul - 14 Jul
The Millerton Inn
Property amenity

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (794 reviews)
  • cleanliness
    Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cosy rooms—all nestled near Ski Butternut.
The price is €190
includes taxes & fees
10 Aug - 11 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (592 reviews)
  • cleanliness
    Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cots in immaculately clean rooms.
The price is €97
includes taxes & fees
20 Jul - 21 Jul
Travelodge by Wyndham Great Barrington Berkshires
Indoor pool

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
Saugerties
7.6 out of 10, Good, (1,002 reviews)
  • cleanliness
    Discover a family oasis with an indoor pool and sauna—create lasting memories at this welcoming Saugerties retreat.
The price is €121
includes taxes & fees
19 Jul - 20 Jul
Howard Johnson by Wyndham Saugerties
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,009 reviews)
  • cleanliness
    Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
The price is €194
includes taxes & fees
19 Jul - 20 Jul
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby lounge

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (28 reviews)
The price is €207
includes taxes & fees
19 Jul - 20 Jul
Element by Marriott 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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Choose what matters most at family-friendly hotels in Hillsdale

Breakfast included
Pool

Top Hillsdale Hotel Reviews

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"Everything was absolutely what we needed and perfect! My only dislike was when we checked in. I just feel if you are the r to great guests and welcome them then you should and give the details of breakfast and just shoe some hospitality is all. The checkout staff was absolutely awesome! I would stay again as this is a great location."
Catherine 1-night trip
Posted 7 hours ago
Quality Inn Lee - Lenox South

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.
What's the best family accommodation in Hillsdale?
Farm House Getaway on beautiful horse farm! is a country house with in-room kitchens and laundry facilities, and it's a top choice on Expedia for families.
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, Roe Jan Brewing Co. and Community Library 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.