
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.


Arthouse Hotel New York City
Manhattan
Price was CA $2,387, price is now CA $1,441 per person
CA $1,441
per person
Mar 14 - Mar 21
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,678 reviews)
Hip boutique hotel with an industrial cozy vibe. Rooms are sumple but have everything you need. The libby bar and cafe are nice. Attached to Serafina restaurant. Great lication overall and parking across the street.
Reviewed on Feb 6, 2026

1 Hotel Central Park
Manhattan
Price was CA $3,267, price is now CA $2,010 per person
CA $2,010
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Excellent stay! Friendly staff, comfortable, beautiful rooms & lobby.
Reviewed on Feb 2, 2026

The Fifth Avenue Hotel
Manhattan
Price was CA $3,505, price is now CA $2,194 per person
CA $2,194
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (159 reviews)
Staff were lovely, helpful and pleasant. Turndown service way too late, though—9:45 might catch some guests sleeping.
Reviewed on Jan 3, 2026

Hyatt Regency Jersey City on the Hudson
Downtown Jersey City
Price was CA $3,189, price is now CA $2,049 per person
CA $2,049
per person
Apr 26 - May 2
just found
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,565 reviews)
We loved to stay here but hotel wifi is too mush slow and some the telephone doesn’t work.all other the staff was so good and nice rooms.
Reviewed on Feb 8, 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 $103 per night from Feb 12 to Feb 13
CA $103
CA $116 total
Feb 12 - Feb 13
includes taxes & fees
7.6/10 Good! (960 reviews)
Super clean! Hotel manager along with all other employees were pleasant and helpful.
Reviewed on Feb 6, 2026

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland NY
9.4/10 Exceptional! (11 reviews)
Great place to stay! Communication was great, beds are SUPER comfortable and the separate heating/cooling in each room is nice. The living room doesn't have enough seeing for it to be the hangout spot, so lots of kitchen conversations :) The piano was a fun addition and we had some fun musical moments. ...
Reviewed on Nov 25, 2025

Courtyard by Marriott Poughkeepsie
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Feb 17 to Feb 18
CA $144
CA $162 total
Feb 17 - Feb 18
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
Very friendly, kind staff and clean room
Reviewed on Feb 2, 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.
What to do in Highland

Bear Mountain State Park+ BeaconTown 1-Day Tour From NY
CA $128
per adult
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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.







