Deals on vacations and trips to Town of Highlands

Save when you book Town of Highlands, NY package deals

Choose two or more items and save on your trip:

Search vacation packages deals in Town of Highlands's top destinations

West Point

Vacations
West Point

Town of Highlands 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
Price was $711, price is now $364 per person
$364
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.
Harpoon House

Harpoon House

3 out of 5
Price was $934, price is now $494 per person
$494
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

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,262, price is now $1,236 per person
$1,236
per person
Oct 26 - Oct 29
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.
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,189, price is now $667 per person
$667
per person
Sep 19 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A coffee shop, limo/town car service, and a snack bar/deli are also on offer.
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
Price was $934, price is now $543 per person
$543
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.

Top Town of Highlands hotels deals

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
$120 nightly
The price is $136 total per night
$136 total
Aug 25 - Aug 26
Total includes taxes and fees
A full-service spa and a restaurant are featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a bar/lounge on site, and concierge services and barbecue grills are also provided.
Pool
Spa
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303, Orangeburg, NY
$80 nightly
The price is $89 total per night
$89 total
Sep 2 - Sep 3
Total includes taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, limo/town car service, and a grocery/convenience store are also offered.
Pool
Parking included
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
$95 nightly
The price is $113 total per night
$113 total
Sep 17 - Sep 18
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
West Gate Inn Nyack

West Gate Inn Nyack

3 out of 5
26 Route 59, Nyack, NY
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $104 total per night
$104 total
Aug 26 - Aug 27
Total includes taxes and fees
A nightclub and a restaurant are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.
Breakfast included
Parking included
Sleepy Hollow Hotel

Sleepy Hollow Hotel

3.5 out of 5
455 S Broadway, Tarrytown, NY
$186 nightly
The price is $213 total per night
$213 total
Sep 7 - Sep 8
Total includes taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Enjoy the 24-hour gym and perks like free self parking.
Pool
Parking included
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd, Suffern, NY
Free Cancellation
$112 nightly
The price is $130 total per night
$130 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features a restaurant, a 24-hour 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 snack bar/deli are also offered.
Pet friendly
Parking included
Don't see what you're looking for?
See all available properties in Town of Highlands
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.

Photos of local treasures

Browse Town of Highlands vacation photos for more inspiration

Town of Highlands
Town of Highlands
Town of Highlands
Photo by Marina Timo
Photo by Marina Timo
Photo by Dan Zheng
Photo by Dan Zheng

Frequently asked questions

How much are vacation packages to Town of Highlands?
Vacation packages, including flights and hotels in Town of Highlands, start from $364. Turn your daydreams into reality and book your dream trip with Travelocity today.
How long should my Town of Highlands vacation be?
Your Town of Highlands getaway can be as short or as long as you want, but the majority of people stay roughly 2 nights. Hoping to veer off the beaten path and uncover some hidden gems? Stay a few more nights and experience another side of this place.
Where can I get the best vacation package deals for Town of Highlands?
Grabbing the best package deal to Town of Highlands is easy with Travelocity. With access to 400 partner airlines and 1,000,000 properties around the world, the choice is yours when it comes to selecting your flights and hotels.
Why should I purchase my Town of Highlands vacation bundle via Travelocity?
Travel is all about making fantastic new memories and leaving all your worries behind — which is why we have a team of experts available round-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our broad range of destinations. So what are you waiting for? There's no time like the present to secure the vacation you've always dreamed of.
Can I save on my Town of Highlands car rental if I bundle it with a hotel or flight?
With a Town of Highlands vacation package, you can combine your hotel, car and flight bookings and save loads. If you can't wait to uncover the best of this impressive area, why not head to Times Square? This renowned sight is 40 mi from Town of Highlands. With your own rental car, you'll be there before you know it.
Which airport is best for Town of Highlands?
John F. Kennedy Intl. Airport (JFK), 50 mi south of central Town of Highlands, is probably where you'll jet into. Your other choices are Liberty Intl. Airport (EWR) (45 mi away from central Town of Highlands) and LaGuardia Airport (LGA) (40 mi away from central Town of Highlands).
What is there to do in Town of Highlands?
While venturing off the beaten track can be rewarding, you shouldn't miss the big-name sights that make a place famous. Michie Stadium and West Point Golf Course are just two of them in Town of Highlands.
Where should I stay when visiting Town of Highlands?
Many travelers opt to check in to the Overlook Lodge at Bear Mountain. It's a terrific base for your Town of Highlands getaway.