Hillsdale Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 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 Vacation

The rich history and welcoming locals are just the beginning of the things Hillsdale has to offer. Experience the sights and sounds of this captivating city the way you want with a customized Hillsdale vacation package. Every trip to Hillsdale just has to include a bit of sightseeing. Where to first? Catamount Aerial Adventure Park and Taconic State Park are key attractions. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Hillsdale vacation is easy with Expedia.

Hillsdale Hotel Deals

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 CA $135 per night from May 20 to May 21
CA $135
CA $151 total
includes taxes & fees
May 20 - May 21
9/10 Wonderful! (233 reviews)
"It’s the perfect place to go for a weekend or weeklong stay and be as isolated as social as you want. The towns nearby are fantastic. Will definitely be back a lot"

Reviewed on May 1, 2024

Life House Berkshires
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 CA $171 per night from May 21 to May 22
CA $171
CA $222 total
includes taxes & fees
May 21 - May 22
8.8/10 Excellent! (880 reviews)
"Great service from the staff and a beautiful place to relax and unwind"

Reviewed on May 10, 2024

The Red Lion Inn
Quality Inn
Quality Inn
2.5 out of 5
170 Housatonic Street, Lee, MA
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from May 19 to May 20
CA $134
CA $150 total
includes taxes & fees
May 19 - May 20
8/10 Very Good! (888 reviews)
"Ok for the money."

Reviewed on May 6, 2024

Quality Inn
See all 1,690 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Hillsdale vacation 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 vacation package.
How do I get a cheap travel package to Hillsdale?
Our Hillsdale vacation 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 vacation 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 favorites with many savvy travelers.
How far in advance should I book my Hillsdale vacation?
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 vacation!
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 vacation package?
Yes — that’s the beauty of an Expedia vacation 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 vacation package?
Whether it’s your hotel, flight or rental car, you can cancel or alter it. Booked your Hillsdale vacation 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.

Discover the most popular places to visit in Hillsdale

Image for Catamount Aerial Adventure Park

Catamount Aerial Adventure Park

You can take time to visit Catamount Aerial Adventure Park during your travels to Hillsdale. Discover the area's mountain views and seek out the hiking trails.

Catamount Aerial Adventure Park
Image for Community Library

Community Library

Community Library is just one of the places to see in Hillsdale, so why not enjoy the other things to explore during your travels? Discover the sunrises while you're in the area.

Community Library
Image for Hillsdale Town Hall

Hillsdale Town Hall

Hillsdale Town Hall is just one of the places to see in Hillsdale, so why not enjoy the other things to explore during your travels? Discover the sunrises while you're in the area.

Hillsdale Town Hall

Other vacations you might like

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