Deals on vacations and trips to Highland

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Highland flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $859, price is now $469 per person
$469
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was $1,941, price is now $985 per person
$985
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. Guests will appreciate perks like free WiFi and a free area shuttle.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,211, price is now $670 per person
$670
per person
Oct 1 - Oct 5
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Free WiFi in public areas, a library, and luggage storage are available at this hotel. Multilingual staff at the 24-hour front desk can provide around-the-clock assistance.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,679, price is now $940 per person
$940
per person
Oct 1 - Oct 5
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A snack bar/deli, dry cleaning, and luggage storage are also on offer.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,598, price is now $901 per person
$901
per person
Oct 1 - Oct 5
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Top Highland hotels deals

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 out of 5
3423 US Highway 9W Highland NY
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $103 total per night
$103 total
Jul 12 - Jul 13
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. A picnic area, laundry facilities, and barbecue grills are also on offer.
Breakfast included
Pet friendly
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $128 total per night
$128 total
Aug 2 - Aug 3
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Breakfast included
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $103 total per night
$103 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Families will appreciate the onsite laundry facilities and babysitting. Business travelers can take advantage of the 24-hour business center.
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave Kingston NY
Get rates
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the indoor pool and perks like free self parking.
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St Gardiner NY
$1,147 nightly
The price is $1,285 total per night
$1,285 total
Jul 19 - Jul 20
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free resort. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like valet parking and WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and concierge services.
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $130 total per night
$130 total
Jul 26 - Jul 27
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 8 conference rooms, free WiFi in public areas, and express check-out. Free self parking, a coffee shop, and a terrace are also offered.
Parking included
Free WiFi
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See all available properties in Highland
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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.

Stay near popular Highland attractions

Franny Reese State Park

You can take time to visit Franny Reese State Park during your travels to Highland. Stroll along the riverfront or discover the mountain views in this family-friendly area.
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Frequently asked questions

How much are vacation packages to Highland?
Travelocity offers package deals to Highland, including hotels and flights, starting at just $469. With all that extra money, you could throw in some cool tours or maybe even tack on some extra days to your exciting adventure.
How long should my Highland vacation be?
Your Highland getaway can be as long as you'd like it to be, but many travelers stay roughly 2 nights. In the mood to venture out and discover some hidden gems? Lock in a few more nights and see a different side of this destination.
Where can I get the best vacation package deals for Highland?
Travelocity will be able to help you snag an awesome Highland package deal. With no less than 400 partner airlines and 1,000,000 properties across the world, you're sure to find the perfect combination.
Why should I book my Highland vacation package with Travelocity?
We offer experiences to suit every type of traveler, exceptional service and customer support available 24/7. In addition to that, we'll match any cheaper price you discover with our Price Match Guarantee.
Can I save money on my Highland car rental if I bundle it with my hotel or flight?
Absolutely — bundle your hotel, flight and car into a Highland vacation package and you'll save a ton. With so many things to do in and around Highland, that rental vehicle will more than come in handy. Once you've slid into the driver's seat, hit the wide open road and head toward Times Square, an unmissable sight about 65 mi from Highland.
Which airport is best for Highland?
Stewart Intl. Airport (SWF) is the main airport if you're flying to Highland. Once you disembark the plane, you'll find yourself 17 mi southwest of the center of town.
What is there to do in Highland?
You'll feel an undeniable magic as you wander through the streets of Highland. Apple Greens Golf Course and Franklin D Roosevelt Library & Museum are just two famous sights that make this city so special, so add them to your must-see list.
Where should I stay when visiting Highland?
The SureStay Plus Hotel by Best Western Highland Poughkeepsie is the first choice of many visitors. Book as soon as possible before it's too late.

Photos of local treasures

Browse Highland vacation photos for more inspiration

A suspension bridge over a river with autumn foliage and distant hills.
A mountainous landscape with a clear sky and scattered clouds.
A large suspension bridge spanning a wide river, surrounded by hills and a train track running parallel to the riverbank.
A suspension bridge over a river with hills in the background.