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.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,904, price is now $1,136 per person
$1,136
per person
Sep 28 - Oct 5
found 1 day 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.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,499, price is now $1,668 per person
$1,668
per person
Sep 24 - Sep 27
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.
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was $4,691, price is now $2,662 per person
$2,662
per person
Nov 3 - Nov 10
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.
5th & 55th Residence Club

5th & 55th Residence Club

5 out of 5
Manhattan
Price was $9,229, price is now $5,318 per person
$5,318
per person
Oct 31 - Nov 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A hair salon, dry cleaning, and luggage storage are also on offer.
2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was $4,318, price is now $2,500 per person
$2,500
per person
Oct 31 - Nov 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

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
$89 nightly
The price is $100 total per night
$100 total
Aug 30 - Aug 31
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
$101 nightly
The price is $117 total per night
$117 total
Sep 7 - Sep 8
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
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $202 total per night
$202 total
Aug 31 - Sep 1
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
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road Poughkeepsie NY
Free Cancellation
$95 nightly
The price is $110 total per night
$110 total
Sep 21 - Sep 22
Total with taxes and fees
A gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A 24-hour business center, a snack bar/deli, and a picnic area are also on offer.
Breakfast included
Parking included
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
$77 nightly
The price is $90 total per night
$90 total
Aug 31 - Sep 1
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
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
$122 nightly
The price is $143 total per night
$143 total
Aug 30 - Aug 31
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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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 $1,136. 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.