Highland Vacation Packages
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Your Highland Vacation
Reserve a Highland vacation package and get set to experience all this city has to offer. Consider basing yourself in the neighborhood of Poughkeepsie Waterfront, which is great for families, history and culture. If sightseeing is on the to-do list during your trip to Highland, swing by well-known attractions like Walkway Over the Hudson State Historic Park, Franklin D Roosevelt Library & Museum and Apple Greens Golf Course. Check out Expedia's wide range of travel options and book your dream vacation to Highland now.
Top Highland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square
Manhattan
Price was CA $3,298, price is now CA $1,968 per person
CA $1,968
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,014 reviews)
We’re a family of 5, the room was roomy in comparison to majority of hotels in NY; the location is perfect; the breakfast buffet had plenty of choices; we loved our stay
Reviewed on May 20, 2026
Highland Hotel Deals
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Jun 18 to Jun 19
CA $127
CA $143 total
Jun 18 - Jun 19
includes taxes & fees
7.8/10 Good! (1,013 reviews)
"Clean room. Friendly staff. Great hot breakfast. Good parking. Stayed here for my daughter's graduation over at New Paltz. Easy 15 minute drive away."
Reviewed on May 18, 2026
Best Western Plus Kingston Hotel And Conference Center
503 Washington Ave Kingston NY
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Jun 17 to Jun 18
CA $164
CA $183 total
Jun 17 - Jun 18
includes taxes & fees
7.4/10 Good! (1,004 reviews)
"The pool was closed so my husband didn’t get to go in"
Reviewed on May 18, 2026
Studio 6 Extended Stay Fishkill Route 9 NY
25 Merritt Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Jun 9 to Jun 10
CA $110
CA $127 total
Jun 9 - Jun 10
includes taxes & fees
6.6/10 (1,001 reviews)
"Was not able to stay there due to accommodations. It’s a good thing though. The place smelt like dog urine and looked run down. Still waiting on my refund and it’s been 5 days."
Reviewed on May 19, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
