Deals on vacations and trips to Highland

Save when you book Highland package deals

Choose two or more items and save on your trip:

Highland flight + hotel vacation packages

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

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,319, price is now $748 per person
$748
per person
Dec 10 - Dec 13
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A steam room is featured at this hotel, along with free WiFi in public areas and dry cleaning. There's luggage storage and multilingual staff can provide around-the-clock assistance.
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Price was $1,835, price is now $892 per person
$892
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate complimentary bicycles and babysitting. Traveling on business? Take advantage of the business center, express check-out, and valet parking.
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was $6,101, price is now $3,590 per person
$3,590
per person
Dec 1 - Dec 7
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 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, limo/town car service, and a snack bar/deli are also on offer.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $3,740, price is now $2,261 per person
$2,261
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
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 William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,739, price is now $1,077 per person
$1,077
per person
Dec 10 - Dec 13
found 2 days ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
This hotel features a bar/lounge, free WiFi in public areas, and a garden. Luggage storage is provided and the front desk is staffed around-the-clock.

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
$80 nightly
The price is $90 total per night
$90 total
Nov 1 - Nov 2
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
$101 nightly
The price is $117 total per night
$117 total
Nov 5 - Nov 6
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
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
$152 nightly
The price is $172 total per night
$172 total
Oct 8 - Oct 9
Total with taxes and fees
A restaurant and a bar/lounge are featured at this inn. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Guests will appreciate freebies like continental breakfast and free self parking.
Breakfast included
Pet friendly
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
1289 Route 300 Newburgh NY
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $80 total per night
$80 total
Oct 19 - Oct 20
Total with taxes and fees
A nightclub and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a lobby fireplace, and a computer station are also offered.
Parking included
Free WiFi
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
$98 nightly
The price is $113 total per night
$113 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an indoor pool and a 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
$1,503 nightly
The price is $1,684 total per night
$1,684 total
Nov 3 - Nov 4
Total with taxes and fees
A full-service spa, 2 outdoor tennis courts, and a 24-hour gym 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. A seasonal outdoor pool, a restaurant, and a 24-hour front desk are also provided.
Pool
Spa
Don't see what you're looking for?
See all available properties in Highland
View all properties
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.
See properties

Frequently asked questions

How much are vacation packages to Highland?
Travelocity offers package deals to Highland, including hotels and flights, starting at just $748. 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.