Roundout Vacations from $479
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The Latest Roundout Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Where to stay in Roundout
Find the best Roundout areas and neighborhoods for the activities you enjoy most. Learn more about Roundout
Hillside
When in Hillside, you can plan a visit to Esopus Creek and Ulster Performing Arts Center, some noteworthy sights in the nearby area.
Roundout Hotel Deals
Kingston Carriage House
85 Abeel St, Kingston, NY
Fully refundableReserve now, pay when you stay
$262 nightly
The price is $296 total per night from Jul 2 to Jul 3
$296 total
Jul 2 - Jul 3
Total includes taxes and fees
9.2/10 Wonderful! (16 reviews)
"one of the best places we’ve stayed at! the poet’s loft is a cozy and quiet two-room suite with two bathrooms. a simple luxury to be enjoyed."
Reviewed on Jun 12, 2025
Best Western Plus Kingston Hotel And Conference Center
503 Washington Ave, Kingston, NY
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $147 total per night from Jul 8 to Jul 9
$147 total
Jul 8 - Jul 9
Total includes taxes and fees
7.8/10 Good! (1,002 reviews)
"Great spot in Kingston, perfect for venturing into the Historic district, or driving over to Woodstock or the Catskills. Check-in took a while due to short staffing."
Reviewed on Jun 21, 2025
Beekman Arms Hotel
6387 MILL ST, Rhinebeck, NY
8.2/10 Very Good! (720 reviews)
"Nice old inn and good breakfast"
Reviewed on Jun 19, 2025
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.
Discover the most popular places to visit in Roundout
Hudson River Maritime Museum
You can study the exhibits at Hudson River Maritime Museum, a museum with a story of its own, during your travels to Kingston. Experience the area's entertainment venues and festivals.
Trolley Museum of New York
You can browse the exhibits at Trolley Museum of New York, a museum with a storied past, during your trip to Kingston. Experience the area's entertainment venues and festivals.
Ashokan Rail Trail- Woodstock Dike Trailhead
You can take time to visit Ashokan Rail Trail- Woodstock Dike Trailhead during your travels to Kingston. Discover the area's mountain views, or seek out its ski slopes.
Things to do
Llama/Alpaca Hike and Farm Tour
$65
per adult
100% of travellers recommend
Meet Our Rescue Animals: Private Tour of A Family-Run Farm
$98
per traveler
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.