Shady Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Shady

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave, Kingston, NY
Fully refundableReserve now, pay when you stay
The price is 3.450.161 ₫ per night from 28 Aug to 29 Aug
3.450.161 ₫
3.864.179 ₫ total
28 Aug - 29 Aug
includes taxes & fees
7.8/10 Good! (1,011 reviews)
"The beds were very comfortable and clean. We slept so well! The room was very clean, and the hotel was nice. Check in was very easy, and the personnel were friendly and courteous."

Reviewed on 19 Aug 2025

Best Western Plus Kingston Hotel And Conference Center
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
9.2/10 Wonderful! (618 reviews)
"Hotel was very clean, grounds looked great and the owner/manager was constantly waiting on guests."

Reviewed on 16 Aug 2025

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Hotel Vienna
Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

2 out of 5
282 Cairo Junction Rd, Catskill, NY
The price is 4.446.897 ₫ per night from 1 Sept to 2 Sept
4.446.897 ₫
5.797.280 ₫ total
1 Sept - 2 Sept
includes taxes & fees
9.4/10 Exceptional! (59 reviews)
"It was just really nice. Cute little (and I do mean little) modern trailer/cabins. Nicely appointed. Good lighting. . We’ll be back."

Reviewed on 18 Aug 2025

Postcard Cabins Eastern Catskills
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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 1null000null000 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.

Popular places to visit

Overlook Mountain Trailhead

Learn about the local history of Woodstock when you take a trip to Overlook Mountain Trailhead. Discover the mountain views while you're in the area.

Overlook Mountain Trailhead

Karma Triyana Dharmachakra Monastery

Learn about the local history of Woodstock with a stop at Karma Triyana Dharmachakra Monastery. Discover the mountain views while you're in the area.

Karma Triyana Dharmachakra Monastery

Byrdcliffe Barn

Byrdcliffe Barn is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Amble around this relaxing area's forests or experience its art scene.

Byrdcliffe Barn