Hillsdale Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Hillsdale Holiday

The rich history and welcoming locals are just the beginning of the things Hillsdale has on offer. Enjoy the sights and sounds of this lively city your way with a customised Hillsdale holiday package. There's plenty to include on your must-do list during a trip to Hillsdale, beginning with popular sights such as Taconic State Park and Catamount Aerial Adventure Park. A few clicks is all it takes to put together a tailor-made Hillsdale holiday on Expedia.

Hillsdale Holiday

Hillsdale Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Lake Taghkanic State Park, Hudson Chatham Winery and Catamount Aerial Adventure Park

Our pick of the best Hillsdale Hotel Deals

The Brooks Motel

The Brooks Motel

2 out of 5
2871 New York 23, Hillsdale, NY
Fully refundableReserve now, pay when you stay
The price is AU$251 per night from 2 Sept to 3 Sept
AU$251
2 Sept - 3 Sept
includes taxes & fees
7.6/10 Good! (95 reviews)
"Decent value for the money I guess. Basic but clean. Thats important. There were issues with a non-working fridge and a dehumidifier that needs to be dumped but other than that all w as fine"

Reviewed on 14 Aug. 2025

The Brooks Motel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (573 reviews)
I’d stay there again
"Everything was nice expect the “last guests” socks we found tangled in the pull out sofa bed."

Reviewed on 17 Aug. 2025

Get rates
Berkshire Mountain Lodge
Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

2 out of 5
282 Cairo Junction Rd, Catskill, NY
The price is AU$339 per night from 20 Aug to 21 Aug
AU$339
20 Aug - 21 Aug
includes taxes & fees
9.4/10 Exceptional! (57 reviews)
"What I like about the property that is was a beautiful area to recharge and refresh your mind, getting away from the city side was soo peaceful I would recommend going back again. The thing I don’t like the cabin that I was staying the stovetop wasn’t working to it’s full potential but it worked ..."

Reviewed on 13 Aug. 2025

Postcard Cabins Eastern Catskills
See all 1,815 properties in Hillsdale
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Hillsdale holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday to Hillsdale costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Hillsdale?
If you'd like to book a cheap Hillsdale holiday package, consider planning a trip in May, September and December. You'll typically find lower prices on accommodation and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Hillsdale?
With a well-planned itinerary, you can easily tick off the main Hillsdale attractions in a handful of days. But if you want to discover hidden spots or go on day tours, think about booking your Hillsdale holiday for longer.
How to find the best Hillsdale package deals?
Begin your search for a Hillsdale package deal by entering your destination and travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Hillsdale package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Hillsdale escape underway.
Is it cheaper to book a Hillsdale holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalised Hillsdale holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Hillsdale?
If you've got your Hillsdale holiday dates locked in, book as soon as you can to bag some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Hillsdale?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Hillsdale.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to set aside for your trip to Hillsdale. Then, select a hotel that fits your budget, whether that's an affordable stay or a swankier getaway.
  3. Decide how many days away: Start by making a list of all the activities and sights you'd like to experience in Hillsdale. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Hillsdale holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.