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.
Newark Hansbury Multi Level House

Newark Hansbury Multi Level House

2 out of 5
Weequahic
Price was $664, price is now $394 per person
$394
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage and barbecue grills are also provided.
Holiday Inn Express New York City Times Square by IHG

Holiday Inn Express New York City Times Square by IHG

3 out of 5
Manhattan
Price was $1,163, price is now $647 per person
$647
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast and free WiFi. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking. Dry cleaning, laundry facilities, and concierge services are also on offer.
The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Save 100% on your flight
Price was $1,459, price is now $835 per person
$835
per person
Jan 8 - Jan 11
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. Families will appreciate the onsite laundry facilities and in-room childcare. WiFi in public areas is free.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,300, price is now $760 per person
$760
per person
Jan 9 - Jan 13
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. WiFi in public areas is free. A 24-hour business center, a terrace, and limo/town car service are also on offer.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was $1,439, price is now $865 per person
$865
per person
Jan 15 - Jan 18
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 library, a computer station, and dry cleaning 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
$80 nightly
The price is $90 total per night
$90 total
Nov 11 - Nov 12
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
$94 nightly
The price is $109 total per night
$109 total
Nov 29 - Nov 30
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
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
Free Cancellation
$98 nightly
The price is $113 total per night
$113 total
Nov 29 - Nov 30
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
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A Poughkeepsie NY
Free Cancellation
$93 nightly
The price is $108 total per night
$108 total
Nov 29 - Nov 30
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and 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
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $134 total per night
$134 total
Dec 8 - Dec 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
The Thayer Hotel at West Point

The Thayer Hotel at West Point

3.5 out of 5
674 Thayer Road West Point NY
$219 nightly
The price is $259 total per night
$259 total
Nov 22 - Nov 23
Total with taxes and fees
Free WiFi in public areas, a terrace, and a computer station are available at this hotel. Traveling on business? Take advantage of the 6 onsite conference rooms. Luggage storage and wedding services are also provided.
Free WiFi
Air conditioning
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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 $394. 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.