Family Hotels & Resorts in Hillsdale from AU$109

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Check availability on Hillsdale Family Hotels

Our top choices for Hillsdale family-friendly hotels

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, (1,001 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
The price is AU$176
includes taxes & fees
11 June - 12 June
Best Western Plus Berkshire Hills Inn & Suites
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, (133 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 AU$150
includes taxes & fees
7 July - 8 July
Spark by Hilton West Coxsackie
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, (583 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 AU$125
includes taxes & fees
9 June - 10 June
Travelodge by Wyndham Great Barrington Berkshires
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (824 reviews)
The price is AU$109
includes taxes & fees
22 June - 23 June
FairBridge Inn Express
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 AU$205
includes taxes & fees
9 June - 10 June
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, (1,003 reviews)
  • cleanliness
    Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
The price is AU$223
includes taxes & fees
11 June - 12 June
The Black Swan Lee - Lenox, an Ascend Collection Hotel
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (666 reviews)
  • cleanliness
    Family-friendly budget escape with free miniature golf and breakfast, minutes from Berkshire Botanical Garden.
The price is AU$113
includes taxes & fees
14 June - 15 June
Econo Lodge Lee - Great Barrington
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.6 out of 10, Excellent, (29 reviews)
The price is AU$385
includes taxes & fees
9 July - 10 July
The Millerton Inn
Interior

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.6 out of 10, Exceptional, (16 reviews)
The price is AU$445
includes taxes & fees
30 June - 1 July
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Deluxe Room, 1 King Bed, Ensuite (2nd Floor)

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (117 reviews)
The price is AU$310
includes taxes & fees
9 June - 10 June
Changing Times Boutique Country Lodging
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

The Red Lion Inn

The Red Lion Inn

8/10 Good
"It is a charming, historic hotel. Dinner in the tavern was delicious and service was very good. The only thing we didn't like was the mattress, which needs to be replaced as it has divits. Other than that, it's a cool place that is fun to explore. Wish we were here longer to try out the pool. We did enjoy getting a cocktail from the bar and sitting in rockers on the front porch, watching the traffic go by."
Nancy 1-night trip
Posted 1 hour ago
The Red Lion Inn

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, Community Library and Ski Butternut 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 Lake Taghkanic State Park and Naumkeag Museum.