Roundout Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ₩234,741 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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
The price is ₩441,959 per night from Jul 28 to Jul 29
₩441,959
₩514,793 total
Jul 28 - Jul 29
includes taxes & fees
9/10 Wonderful! (17 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
The price is ₩181,213 per night from Jul 29 to Jul 30
₩181,213
₩202,957 total
Jul 29 - Jul 30
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"We had a great stay. Breakfast was a good with several options."
Reviewed on Jul 15, 2025
Holiday Inn Express Poughkeepsie by IHG
2750 South Road, Poughkeepsie, NY
Fully refundable
The price is ₩145,114 per night from Aug 11 to Aug 12
₩145,114
₩168,514 total
Aug 11 - Aug 12
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"Clean staff was friendly"
Reviewed on Jul 21, 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
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.