Highland Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Karen Wirtz
Top hotels in Highland
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
The price is 2.102.912 ₫ per night from 4 Jan to 5 Jan
2.102.912 ₫
2.355.260 ₫ total
4 Jan - 5 Jan 2026
includes taxes & fees
7.6/10 Good! (949 reviews)
Nice staff, large rooms
Reviewed on 8 Dec 2025
Residence Inn by Marriott Kingston
800 Frank Sottile Boulevard Kingston NY
Fully refundableReserve now, pay when you stay
The price is 3.000.024 ₫ per night from 1 Jan to 2 Jan
3.000.024 ₫
3.360.027 ₫ total
1 Jan - 2 Jan 2026
includes taxes & fees
8.8/10 Excellent! (802 reviews)
Staff was very kind and courteous
Reviewed on 24 Dec 2025
Hampton Inn & Suites Poughkeepsie
2361 South Rd Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is 2.569.379 ₫ per night from 2 Jan to 3 Jan
2.569.379 ₫
2.983.693 ₫ total
2 Jan - 3 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
This place is great it’s clean, great staff, and nice breakfast options. Will definitely be coming back!
Reviewed on 23 Dec 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.
Popular places to visit
Franklin D Roosevelt Library & Museum
You can study the exhibits at Franklin D Roosevelt Library & Museum, a museum with a story of its own, during your holiday in Highland. While you're in the area, stroll along the riverfront.
Apple Greens Golf Course
Enjoy a round of golf in Highland at Apple Greens Golf Course. Wander the riverfront in this family-friendly area.
