Shady Vacations from $643
Book a Hotel + Flight or Car together to unlock savings
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.
Eastwind Windham
$676
per person
Dec 9 - Dec 12
found 12 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Hudson (HCC)
9.2/10 Wonderful! (120 reviews)
Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay.
Reviewed on Oct 20, 2026
Shady Hotel Deals
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$169 nightly
$191 total
Nov 3 - Nov 4
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
7433 Main St Hunter NY
Fully refundableReserve now, pay when you stay
$135 nightly
$146 total
Nov 19 - Nov 20
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
"Surprised that there were additional "facility" charges when we checked in. The reception was argumentative, never said thank you, and 2 of the 3 front desk staff were generally indifferent. Breakfast was surprisingly poor for an expensive hotel. There was no hot food, just what one could get from ..."
Reviewed on Oct 20, 2026
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
282 Cairo Junction Rd Catskill NY
$201 nightly
$217 total
Nov 19 - Nov 20
Total with taxes and fees
9.6/10 Exceptional! (325 reviews)
"10/10 experience! Can’t wait to go back! One overnight stay isn’t enough stay for multiple days!!!!"
Reviewed on Oct 19, 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.