Roundout Vacations from $634
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The Latest Roundout Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Prospect Berkshires
Price was $1,161, price is now $634 per person
$634
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (2 reviews)
Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway
Reviewed on Jun 23, 2025
The Perch Hotel
Save 100% on your flight
Price was $2,296, price is now $1,400 per person
$1,400
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (14 reviews)
Exceptional view. The sunrise from the valley view is incredible
Reviewed on Aug 16, 2025
Kingston Carriage House
Roundout
Save 100% on your flight
Price was $1,322, price is now $927 per person
$927
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.2/10 Wonderful! (21 reviews)
I liked the record player and the room was clean and comfy. Coffee and pastries were waiting by the door in the morning. Checking in, the battery was dead in the room lock. Had to wait 30 mins for service to arrive. The shower floor was dangerously slippery! An accident waiting to happen. Was unable to connect to Wi-Fi after multiple tries.
Reviewed on Aug 3, 2025
Urban Cowboy Lodge
Save 100% on your flight
Price was $1,427, price is now $1,091 per person
$1,091
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.2/10 Wonderful! (161 reviews)
The staff here was amazing, had a great one night getaway and I wished we stayed longer!
Definitely would come back! Service A plus!
Food A plus! Scenery outstanding! Definitely recommend for a good wind down from ones busy day to day.
Reviewed on Aug 15, 2025
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
$224 nightly
The price is $250 total per night from Sep 2 to Sep 3
$250 total
Sep 2 - Sep 3
Total with taxes and fees
9/10 Wonderful! (22 reviews)
"I liked the record player and the room was clean and comfy. Coffee and pastries were waiting by the door in the morning. Checking in, the battery was dead in the room lock. Had to wait 30 mins for service to arrive. The shower floor was dangerously slippery! An accident waiting to happen. Was unable ..."
Reviewed on Aug 3, 2025
Quality Inn Poughkeepsie
536 Haight Ave, Building A, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $115 total per night from Sep 8 to Sep 9
$115 total
Sep 8 - Sep 9
Total with taxes and fees
7.6/10 Good! (403 reviews)
"Overall good stay"
Reviewed on Aug 24, 2025
Wildflower Farms, Auberge Resorts Collection
2702 Main St, Gardiner, NY
$1,050 nightly
The price is $1,176 total per night from Sep 22 to Sep 23
$1,176 total
Sep 22 - Sep 23
Total with taxes and fees
9.4/10 Exceptional! (52 reviews)
"Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch"
Reviewed on May 15, 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
$67
per adult
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.