Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Save up to $603 by booking Flight + Hotel.

Search 321,000 hotels and 400 airlines worldwide.

Get the price Guarantee available for your trip.


Highland

Poughkeepsie has around 33,000 residents.

Packages in Highland

Save money with your Expedia package deal. If you'd like to save some extra money, consider how easy it is to combine your flight and lodging bookings with us. Spend a little more in Highland with the extra money.

Save up to $603 when you book your Highland package deal.

You don't need to frantically look around different websites for your travel bookings. With approximately 400 partner airlines and 321,000 hotels around the world our thorough database has got it all.

You will receive some of the best prices for your vacation with Expedia.

You can postpone your travel itineraries with us because we do not charge cancellation fees for almost all of our reservations.

Highland Vacation Packages

If you decide to base your trip in Highland, you're sure to meet quite a few of them! Highland lies 17 miles to the north of Stewart International Airport and 4 miles from the city's heart.

When you're settled in, it's time to go to a few close tourist hotspots. Start at Vassar College or Frances Lehman Loeb Art Center. Stop at Mid-Hudson Heritage Center and McCann Ice Arena if you have the time. Spread your wings and explore the neighboring areas too, including Clintondale and Poughkeepsie Waterfront.

Ask about tours and one-off events at Home of Franklin D. Roosevelt National Historic Site, Mid-Hudson Children's Museum, Storm King Art Center and Dia Beacon. You'll find something everyone will enjoy.

Book your pass, locate your seat and get set for a top show at a local venue, such as Chance Theater and Bardavon 1869 Opera House.

Order a coffee to go and unwind in the sunshine at a nearby park, including Walkway Over the Hudson State Historic Park and The Waterfront.

Poughkeepsie Bridge, Mid-Hudson Bridge, Culinary Institute of America and Lyndhurst Castle can give you a vision of the past.

There are very few hotels in Highland on the Expedia lodging page, so it's a good idea to reserve a room early.

Some of the lodgings that might suit your needs in Highland are the Buttermilk Falls Inn and Residence Inn by Marriott Poughkeepsie.


Top Hotel Deals

See all 160 Hotels in Highland
$62
Super 8 Highland NY

Super 8 Highland NY

3423 US Highway 9W, Highland
3.2
of 5, from 66 reviews
2.0 out of 5.0

Situated in Highland, this hotel is 2.6 mi (4.1 km) from Walkway Over the Hudson State Historic Park and within 6 mi (10 km) of West Park Winery and Apple Greens Golf Course. Mid-Hudson Bridge and Bardavon 1869 Opera House are also within 9 mi (15 km).

$75
Americas Best Value Inn

Americas Best Value Inn

3497 Us Highway 9w, Highland
3.1
of 5, from 60 reviews
2.0 out of 5.0

Situated in Highland, this motel is within 3 mi (5 km) of Walkway Over the Hudson State Historic Park, Poughkeepsie Bridge, and Mid-Hudson Bridge. Bardavon 1869 Opera House and McCann Ice Arena are also within 6 mi (10 km).

$90
Atlas Motor Lodge

Atlas Motor Lodge

125 Tillson Avenue EXT, Highland
3.2
of 5, from 33 reviews
2.0 out of 5.0

Situated in Highland, this motel is within 2 mi (3 km) of Walkway Over the Hudson State Historic Park, Poughkeepsie Bridge, and Mid-Hudson Bridge. Mid-Hudson Children's Museum and Bardavon 1869 Opera House are also within 3 mi (5 km).

$130
Stonegate Bed and Breakfast

Stonegate Bed and Breakfast

34 North Road, Highland
5.0
of 5, from 11 reviews
3.5 out of 5.0

Situated in a rural location, this bed & breakfast is within 3 mi (5 km) of Walkway Over the Hudson State Historic Park, Poughkeepsie Bridge, and Mid-Hudson Children's Museum. Mid-Hudson Bridge is 2.8 mi (4.6 km) away.

$110
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

100 Westage Business Center Dr., Fishkill
4.5
of 5, from 290 reviews
3.0 out of 5.0

Situated in Fishkill, this hotel is within 1 mi (2 km) of Van Wyck Homestead Museum and Blodgett Memorial Library. Fishkill Golf Course and SplashDown Beach are also within 2 mi (3 km).

$85
Americas Best Value Inn-New Paltz

Americas Best Value Inn-New Paltz

7 Terwilliger Ln, New Paltz
3.8
of 5, from 175 reviews
2.0 out of 5.0

Situated in New Paltz, this motel is within 2 mi (3 km) of State University of New York-New Paltz, G. Steve Jordan Gallery, and Loren Campbell Memorial Field. New Paltz Golf Course and Testimonial Gateway are also within 3 mi (5 km).

$72
Super 8 Kingston

Super 8 Kingston

487 Washington Ave, Kingston
3.0
of 5, from 165 reviews
2.0 out of 5.0

Situated in Kingston, this motel is within a 15-minute walk of Senate House State Historic Site, Forsyth Park, and Volunteer Fireman's Hall and Museum of Kingston. Old Dutch Church and Ulster Performing Arts Center are also within 2 mi (3 km).

Top Flight + Hotel Deals

Top Deals on Flights

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.