Shady Vacations from $642
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Your Shady Vacation
Make planning your travels easier by reserving a vacation package to Shady. Let us take care of the minutiae, so you can focus on enjoying everything this neighborhood 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 vacation looks like, you can make it a reality with Expedia.
The Latest Shady vacation packages
Price found within the past 48 hours. Click for updated prices.
Wylder Hotel Windham
Save 100% on your flight
Price was $1,205, price is now $957 per person
$957
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
8.8/10 Excellent! (100 reviews)
Our stay was ok.
The staff was very responsive when we contacted the front desk, however we tried not to complain when things were not done or not working. The pool was lovely, however staff were power washing the fences on two days when the pool was open! Why this wasn't done in the Spring is suprising.The AC in the room was leaking water. A staff person adjusted it when we contacted the front desk.
One day, garbage was not taken, the bed was not made and towels were not changed until we call the front desk later in the day.
We had continuous difficulty with the TV streaming and had 3 different staff people help with the rebooting and connectivity although it was spotty at best most times. Cable TV would be a better option.
The $50.00 daily fee did not benefit us as we only used the pool. One staff person indicated that this fee could possibly be refunded, but it was not. Breakfast options were limited. Accommodations were pricy.
Thank goodness the staff was friendly and helpful, especially with no elevators!
Reviewed on Jul 5, 2026
Shady Hotel Deals
Best Western Plus Kingston Hotel And Conference Center
503 Washington Ave Kingston NY
7.4/10 Good! (1,005 reviews)
"This is an aging property, poorly designed and in need of replacement, not a touch up, not a redecorating or renovation, replacement. The facility surrounds a pool that adds an uncomfortable level of humidity to the entire building. The room AC's can't keep up, particularly on hot days. The cleaning ..."
Reviewed on Jul 8, 2026
AutoCamp Catskills
882 NY-212 Saugerties NY
$186 nightly
The price is $209 total per night from Aug 3 to Aug 4
$209 total
Aug 3 - Aug 4
Total with taxes and fees
9/10 Wonderful! (525 reviews)
"The AC was too noisy and can’t fall asleep"
Reviewed on Jul 8, 2026
Hunter Lodge, a Bluebird by Lark
7433 Main St Hunter NY
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $163 total per night from Aug 3 to Aug 4
$163 total
Aug 3 - Aug 4
Total with taxes and fees
9.2/10 Wonderful! (998 reviews)
"This lodge is well maintained and very beautiful. Spacious room and spotless. Shower/ toilet are is very tight."
Reviewed on Jul 9, 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.
Find the Best Shady Vacation Packages
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
