Shady Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 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 easyPackages with flights are ATOL protected
Your Shady Holiday
Reserving a tailor-made Shady holiday package is a wonderful way to become familiar with this neighbourhood. From its hot spots to its lesser-known gems, there's plenty to discover. Some top nearby attractions to check out during your trip to Shady include Overlook Mountain Trailhead, Woodstock Music Shop and Karma Triyana Dharmachakra Monastery. Stop dreaming and start doing. When you're ready to lock in your next holiday to Shady, Expedia will help get you there.
Top hotels in Shady
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
£134
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
Fully refundableReserve now, pay when you stay
£116
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
£165
7 Sept - 8 Sept
includes taxes & fees
9.6/10 Exceptional! (286 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 travel package cost?
We make it simple to travel somewhere new, with Shady travel packages starting from as low as . You'll have the flexibility to bundle your favourite hotels, airlines and car rental. For the ultimate escape, why not add some experiences and tours to your itinerary?
If I'm not able to travel, can I cancel my Shady travel package?
Yes, you can cancel your Shady booking if your travel plans have changed. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.
How do I get a cheap travel package to Shady?
It's easy. Just bundle. Flights, hotels and rental cars — combine whatever you need into a Shady travel package to save loads of cash. Score even bigger bargains when you add extras such as tours or experiences to your booking. But that's not the only impressive part. You have the freedom to customize your trip your way. We offer more than 550 partner airlines and 1,000,000 properties throughout the world, so that everyone has a chance to travel and fulfil those holiday dreams.
Does Expedia offer Book Now, Pay Later Shady holidays?
Yes. Expedia has teamed up with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply click on the payment plan that suits best during checkout and take away the stress of budgeting for your next trip. Remember to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:
- Pay monthly holidays: Klarna has easy monthly payment plans that suit all types of budgets, so you can lock in that well-earned holiday sooner.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your trip across multiple transactions.
- Low deposit holidays: Hitting the "book now" button is easier with this payment option. Just put down a small deposit on your holiday and then start packing your suitcase.
Where should I stay in Shady?
A holiday in Shady wouldn't be complete without visiting Woodstock Public Library, Woodstock Music Shop and Karma Triyana Dharmachakra Monastery. Spend your nights near these top attractions and make sightseeing a breeze.
What are the top hotels in Shady?
Book a room at The Woodstock Inn on the Millstream. It's one of the area's most sought-after hotels. Another highly rated option in Shady is Twin Gables of Woodstock.
How far in advance should I book my Shady holiday?
While prices fluctuate, we generally suggest booking your spot as early as possible. Most international airfares are found on Expedia up to a year in advance. If you're booking late, you might still get lucky. Low prices to Shady sometimes appear only weeks before departure.
What does an Expedia Shady travel package include?
It comes down to what you're after. If you're travelling by yourself, you might decide to combine flights and hotels. Bringing the entire family to Shady? A travel package that includes hotels, rental cars and flights might suit you better. Expedia gives you the flexibility to build your own travel package.
What should I know before booking a Shady travel package?
You can save big by combining your hotels, flights and rental cars. Once you've made your booking, you can add on day tours or experiences. Your next awesome holiday is only a few clicks away.
Can I choose my airline with a Shady Expedia travel package?
Yes, so take your pick! We have access to over 550 airlines throughout the world, so you can customize your Shady adventure according to your budget and travel needs.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
