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 2.102.832 ₫ per night from 4 Jan to 5 Jan
2.102.832 ₫
2.355.174 ₫ total
4 Jan - 5 Jan 2026
includes taxes & fees
7.6/10 Good! (948 reviews)
Nice staff, large rooms
Reviewed on 8 Dec 2025
Hampton Inn & Suites Poughkeepsie
2361 South Rd Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is 2.675.709 ₫ per night from 9 Jan to 10 Jan
2.675.709 ₫
3.107.168 ₫ total
9 Jan - 10 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
Very clean. Friendly staff. Breakfast was excellent. Room was great. What a surprise that Santa was there for breakfast. Would definitely go back.
Reviewed on 16 Dec 2025
Quality Inn Poughkeepsie
536 Haight Ave, Building A Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is 2.438.085 ₫ per night from 29 Dec to 30 Dec
2.438.085 ₫
2.831.225 ₫ total
29 Dec - 30 Dec
includes taxes & fees
7.8/10 Good! (500 reviews)
Room was clean. Staff was kind. Good complimentary breakfast
Reviewed on 23 Nov 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.
