
Roundout Vacations from $634
Book a Hotel + Flight or Car together to unlock savings
The Latest Roundout Vacation Packages

Prospect Berkshires
Reviewed on Jun 23, 2025

The Perch Hotel
Reviewed on Aug 16, 2025

Kingston Carriage House
Reviewed on Aug 3, 2025


Urban Cowboy Lodge
Reviewed on Aug 15, 2025
Where to stay in 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
Reviewed on Aug 3, 2025

Quality Inn Poughkeepsie
Reviewed on Aug 24, 2025

Wildflower Farms, Auberge Resorts Collection
Reviewed on May 15, 2025
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
