Hillsdale Vacations

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to NT$5,755 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

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 NT$3,204 per night from May 6 to May 7
NT$3,204
per night
May 6 - May 7
9/10 Wonderful! (232 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 2024/5/1

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 NT$3,830 per night from May 6 to May 7
NT$3,830
per night
May 6 - May 7
8.8/10 Excellent! (872 reviews)
"The most quaint and cozy New England Inn, with multiple dining options, two boutiques, heated swimming pool, close to all the Berkshires has to offer, everything is perfect!"

Reviewed on 2024/5/2

The Red Lion Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
Fully refundableReserve now, pay when you stay
The price is NT$3,466 per night from May 8 to May 9
NT$3,466
per night
May 8 - May 9
8.8/10 Excellent! (1,001 reviews)
"Just a nice, cozy and very clean little hotel. We would stay there again if in the area."

Reviewed on 2024/5/1

The Black Swan Lee - Lenox, Ascend Hotel Collection
See all 1,715 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.

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.
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.