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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $842, price is now $485 per person
$485
per person
May 5 - May 8
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,140, price is now $1,268 per person
$1,268
per person
May 5 - May 8
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.
The Ridge Hotel

The Ridge Hotel

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,870, price is now $1,143 per person
$1,143
per person
Jun 10 - Jun 16
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
A rooftop terrace is featured at this hotel, along with free WiFi in public areas and a garden. A computer station and a safe deposit box are also provided.
Madison Hotel

Madison Hotel

4 out of 5
Save 100% on your flight
Price was $1,972, price is now $1,273 per person
$1,273
per person
Jun 20 - Jun 27
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,551, price is now $1,015 per person
$1,015
per person
May 3 - May 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
This property 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.

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
$84 nightly
The price is $94 total per night
$94 total
Apr 7 - Apr 8
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
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
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $107 total per night
$107 total
Apr 12 - Apr 13
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a garden, and a grocery/convenience store are also offered.
Pet friendly
Parking included
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $134 total per night
$134 total
Apr 9 - Apr 10
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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
Apr 8 - Apr 9
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.
Pool
Spa
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
800 Frank Sottile Boulevard Kingston NY
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $142 total per night
$142 total
Apr 19 - Apr 20
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.
Breakfast included
Pet friendly
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3 out of 5
25 OLD VINEYARD PLACE Hyde Park NY
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $163 total per night
$163 total
Apr 19 - Apr 20
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the laundry service. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
Breakfast included
Pet friendly
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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.

Popular places to visit

Highland, New York: Ruins of the Dr. Charles H. Roberts estate, in Franny Reese State Park.

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.

Franny Reese State Park

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 travels to Highland. While you're in the area, stroll along the riverfront.

Franklin D Roosevelt Library & Museum

Apple Greens Golf Course

4.5/5(2 reviews)

Enjoy a round of golf in Highland at Apple Greens Golf Course. Wander the riverfront in this family-friendly area.

Apple Greens Golf Course

Frequently asked questions

How much are vacation packages to Highland?
Travelocity offers package deals to Highland, including hotels and flights, starting at just $485. 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

panoramic view of mid hudson bridge over hudson river valley (poughkeepsie, upstate new york) sunny day train station wide angle sun glare crossing suspension small town travel metro north
Overview of Cold Spring and Hudson Highlands State Park in Fall, New York - October 2024
Highland
Highland