Hillsdale Holidays

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Our pick of the best Hillsdale Hotel Deals

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is NZ$217 per night from 25 Jun to 26 Jun
NZ$217
per night
25 Jun - 26 Jun
9/10 Wonderful! (270 reviews)
"Very pleasant place to stay rooms and nice and clean. Staff is very nice."

Reviewed on 21 Jun. 2024

Life House Berkshires
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
The price is NZ$363 per night from 26 Jun to 27 Jun
NZ$363
per night
26 Jun - 27 Jun
8.8/10 Excellent! (903 reviews)
"Loved The Red Lion Inn Gorgeous inside and out , My bucket list wish finally made come true !! Will be back for sure . Great staff , very attentive and polite . Loved the 2 kitties hanging out , Joyful stay !"

Reviewed on 22 Jun. 2024

The Red Lion Inn
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$228 per night from 25 Jun to 26 Jun
NZ$228
per night
25 Jun - 26 Jun
9/10 Wonderful! (1,001 reviews)
Pleasantly surprised
"We had a good experience here! The staff was AWESOME! They were very helpful in checking in and gave us good info. They have a bar but it was not open during the times we were in and out. The breakfast was good and we enjoyed the omelet. Its only on the weekend--wish it was every day! The pool was ..."

Reviewed on 15 Jun. 2024

The Yankee, Trademark Collection by Wyndham
See all 1,678 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 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.
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.

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

More holiday ideas

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