Shady Vacations from $797
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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.
The Haüs Windham
$983
per person
Oct 23 - Oct 26
found 14 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
7.8/10 Good! (34 reviews)
Firstly I would like to say communication with the staff is extremely difficult. Constantly having to call multiple times to get to someone. For example, the code given for room wasn’t correct and communication took forever. There was no toiletries whatsoever and since communication was so hard it forced us to buy our own paper towels, towels, rags, etc. The property was nice but it was clear no housekeeping had been in there before we came. The nature was probably the only thing that made up for all the inconveniences.
Reviewed on Aug 13, 2026
Shady Hotel Deals
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
$175 nightly
$198 total
Sep 20 - Sep 21
Total with taxes and 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 Aug 26, 2026
Hunter Lodge, a Bluebird by Lark
7433 Main St Hunter NY
$147 nightly
$158 total
Sep 7 - Sep 8
Total with taxes and fees
9.2/10 Wonderful! (1,014 reviews)
"Very cool place to stay...breakfast could have been better...maybe some hot food options"
Reviewed on Aug 24, 2026
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
282 Cairo Junction Rd Catskill NY
$209 nightly
$226 total
Sep 7 - Sep 8
Total with taxes and fees
9.6/10 Exceptional! (284 reviews)
"We really enjoyed staying at postcard, room were clean and everything was so organized and clean. Really like we can cook our food. Only thing is it will be great if you can put small mirror in the bathroom or room."
Reviewed on Aug 23, 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.
