Hillsdale Holidays

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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.

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$369 per night from 25 Nov to 26 Nov
AU$369
includes taxes & fees
25 Nov - 26 Nov
8.8/10 Excellent! (1,001 reviews)
"Didn’t like that there are no trays in shower to hold any soaps or bottles while washing… nothing!!! Tub too high for elderly with slightest arthritis. No curtain on shower bathroom window. Took quite a while to get hot water to wash hands in sink. However, the inn is filled with amazing collectibles. ..."

Reviewed on 20 Nov. 2024

The Red Lion Inn
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$205 per night from 25 Nov to 26 Nov
AU$205
includes taxes & fees
25 Nov - 26 Nov
9/10 Wonderful! (442 reviews)
"Staff were very friendly and the rooms were decorated adorably! We absolutely enjoyed our stay!"

Reviewed on 20 Nov. 2024

Life House Berkshires
Howard Johnson by Wyndham Saugerties
Howard Johnson by Wyndham Saugerties
2 out of 5
2764 Route 32, Saugerties, NY
Fully refundableReserve now, pay when you stay
The price is AU$187 per night from 24 Nov to 25 Nov
AU$187
includes taxes & fees
24 Nov - 25 Nov
7.4/10 Good! (1,000 reviews)
"Location is 30 minutes drive to Catskill State Park"

Reviewed on 12 Nov. 2024

Howard Johnson by Wyndham Saugerties
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.

Frequently asked questions

How much does a Hillsdale holiday package cost?
Explore the best of Hillsdale from as low as . Choose from a great selection of rental cars, hotels and flights to suit your budget. You can pick up even better deals when you add some tours or activities to your holiday package.
How do I get a cheap travel package to Hillsdale?
Our Hillsdale holiday packages offer plenty of savings for the savvy explorer. For the best deals, simply combine your flights, hotels and tours into a handy package. But great bargains are just the beginning of your next memorable adventure. When you book with Expedia, you’ll have more than 550 airlines and 1 000 000 hotels globally to choose from. No matter your style or budget, there’s a holiday package with your name on it.
Where should I stay in Hillsdale?
Hillsdale is home to a number of terrific places to see, like Catamount Aerial Adventure Park. Stay someplace near this attraction and make sightseeing easier.
What are the top hotels in Hillsdale?
If this will be your first time in Hillsdale, reserve a room at Cabin - Ideal Location For Summer And Winter Activities With Plenty Of Outdoor Space or Holiday House Motel Hillsdale. Both hotels will make you feel at home and are favourites with many savvy travellers.
How far in advance should I book my Hillsdale holiday?
Reward yourself with the biggest variety and the lowest prices by booking your Hillsdale adventure early. Air carriers typically release tickets anywhere up to 12 months prior to departure, so start your planning as soon as you can. That said, Expedia is constantly working to give you the best deals around, so it’s always a good time to book your dream holiday!
What does an Expedia Hillsdale travel package include?
Choose from a combination of rental cars, hotels and flights. Once you’ve made your booking, you can add experiences and tours. Want to pick your fare class? That’s easy to do too. The choice is all yours when it comes to planning your perfect Hillsdale getaway.
What should I know before booking a Hillsdale travel package?
An Expedia travel package can be tailored to your budget and is a terrific way to make your budget go further. What you include is up to you. Rental cars, hotels and flights — mix and match whatever combination suits your style.
Can I choose my airline with a Hillsdale Expedia holiday package?
Yes — that’s the beauty of an Expedia holiday package. You’re in charge! We have more than 550 airline partners around the world, so you have loads of choice when arranging your Hillsdale escape.
If I'm not able to travel, can I cancel my Hillsdale holiday package?
Whether it’s your hotel, flight or rental car, you can cancel or alter it. Booked your Hillsdale holiday package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may incur a fee from your hotel, airline or car rental company. For more details, head to our Customer Service Portal. We’re here to help you each step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.