Shady Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Shady Holiday
Make planning your travels easier by reserving a holiday package to Shady. Let us take care of the minutiae, so you can focus on enjoying everything this neighbourhood can offer. Want to explore the sights during your trip to Shady? Pencil in a visit to nearby attractions such as Overlook Mountain Trailhead, Woodstock Music Shop and Karma Triyana Dharmachakra Monastery. No matter what your ideal Shady holiday looks like, you can make it a reality with Expedia.
Shady Holiday
Our pick of the best Shady Hotel Deals
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
AU$254
3 Sept - 4 Sept
includes taxes & fees
8.2/10 Very good! (987 reviews)
"I have a habit of calling ahead a day or two before my arrival to make sure my reservation is confirmed. I made numerous attempts to to so and no one was answering the phones? It took from 1.30pm - 8.30pm to reach someone.... Other than the trash can missed being empty, all was very nice. I will ..."
Reviewed on 26 Aug 2026
Hunter Lodge, a Bluebird by Lark
7433 Main St Hunter NY
AU$221
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (1,015 reviews)
"Our room has a great view of the mountains. The staff is very friendly."
Reviewed on 26 Aug 2026
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
282 Cairo Junction Rd Catskill NY
AU$303
24 Sept - 25 Sept
includes taxes & fees
9.6/10 Exceptional! (285 reviews)
"Clean room, staff was easily accessible, wifi was good."
Reviewed on 26 Aug 2026
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 Shady holiday package cost?
Perhaps less than you might think — from just , actually! By bundling flights, hotels and car rentals into your own customized holiday package, your Shady escape is just a few clicks away.
How do I get a cheap travel package to Shady?
Simply by bundling. Hotels, rental cars and flights — combine whatever you need into a Shady holiday package to save a ton of cash. Score even more discounts when you add extras such as sightseeing tours to your booking. But that's not the only impressive part. You have the freedom to tailor your holiday your way. We offer more than 550 partner airlines and 1 000 000 properties around the world, so that everyone has an opportunity to travel and live out those holiday dreams.
Where should I stay in Shady?
With loads to explore in Shady, it's a good idea to book a room in a hotel close to its attractions. Overlook Mountain Trailhead, Karma Triyana Dharmachakra Monastery and Woodstock Music Shop are some good ones to put on your itinerary.
How far in advance should I book my Shady holiday?
Travellers can normally browse international airfares on Expedia up to 12 months prior to departure. Booking late? With a bit of luck, it's still possible to purchase a cheaper ticket only weeks before your journey.
What does an Expedia Shady travel package include?
Packages include flights, rental cars and hotels, but you can combine any of them to create your ideal Shady holiday. You can also add on a few tours and activities once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Shady travel package?
When you book your flights, hotels and car rentals together, you'll nab fantastic discounts. Whether you're organising an island getaway in a villa or would rather stay in a convenient hotel in the city, Expedia will make it happen for less.
Can I choose my airline with a Shady Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You get to decide. We have access to more than 550 partner airlines all over the world, so you have options galore when creating your Shady adventure.
If I'm not able to travel, can I cancel my Shady holiday package?
We totally understand — life sometimes gets in the way of your plans. If you've booked a Shady holiday package and need to change or cancel it, we're here to help. We suggest browsing our Customer Service Portal first for information. But generally, if you've taken out your package in the last 24 hours, you may be able to cancel or change your itinerary free of charge. If it's more than 24 hours, your hotel, airline or car rental company may impose a fee.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
