Deals on vacations and trips to Highland
Save when you book Highland package deals
Highland flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel
Save 100% on your flight
per person
Nov 4 - Nov 7
found 1 day 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.
Sound View Greenport
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.
The Harbor Front Inn
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a 24-hour gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free continental breakfast each morning.
Harpoon House
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This bed & breakfast features a restaurant and 3 bars/lounges. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a terrace, and a garden are also on offer.
1 Hotel Brooklyn Bridge
Save 100% on your flight
per person
Sep 21 - Sep 23
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.
Top Highland hotels deals
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W, I-87 Exit 18 to I-9W, Highland, NY
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $99 total per night
$99 total
Sep 1 - Sep 2
Total includes 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
The Crossroads Hotel, Newburgh
5 Lakeside Rd, Newburgh, NY
$95 nightly
The price is $113 total per night
$113 total
Sep 15 - Sep 16
Total includes taxes and fees
A gym is featured at this hotel, along with free self parking. WiFi in public areas is free. A fireplace in the lobby is provided and the front desk is staffed around-the-clock.
Parking included
Free WiFi
Wildflower Farms, Auberge Resorts Collection
2702 Main St, Gardiner, NY
$1,043 nightly
The price is $1,168 total per night
$1,168 total
Sep 1 - Sep 2
Total includes 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
Quality Inn Poughkeepsie
536 Haight Ave, Building A, Poughkeepsie, NY
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $120 total per night
$120 total
Sep 9 - Sep 10
Total includes 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.
Holiday Inn Express Poughkeepsie by IHG
2750 South Road, Poughkeepsie, NY
Free Cancellation
$109 nightly
The price is $127 total per night
$127 total
Aug 24 - Aug 25
Total includes 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
Best Western Plus Kingston Hotel And Conference Center
503 Washington Ave, Kingston, NY
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $147 total per night
$147 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and free perks like buffet breakfast and free self parking.
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
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.
Apple Greens Golf Course
Enjoy a round of golf in Highland at Apple Greens Golf Course. Wander the riverfront in this family-friendly area.
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.
Frequently asked questions
Photos of local treasures
Browse Highland vacation photos for more inspiration
