Deals on vacations and trips to Orange County
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Orange County flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Sheraton New York Times Square Hotel
Manhattan
Price was $683, price is now $345 per person
$345
per person
Mar 12 - Mar 15
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 business center and free WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.
INNSiDE by Meliá New York Nomad
Manhattan
Price was $809, price is now $355 per person
$355
per person
Mar 12 - Mar 15
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 and free WiFi in public areas. A terrace, limo/town car service, and a picnic area are also on offer.
Topping Rose House
Save 100% on your flight
Price was $1,691, price is now $783 per person
$783
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free valet parking. Enjoy the gym and perks like free self parking and a free area shuttle.
Harpoon House
Price was $1,204, price is now $613 per person
$613
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Sound View Greenport
Save 100% on your flight
Price was $747, price is now $390 per person
$390
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Top Orange County hotels deals
Hampton Inn Harriman Woodbury
60 Centre Dr Central Valley NY
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $120 total per night
$120 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free train station pick-up. Free perks include on-the-go breakfast, free self parking, and a shopping center shuttle.
Pool
Breakfast included
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $115 total per night
$115 total
Jan 12 - Jan 13, 2026
Total with 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
Holiday Inn Express Hotel & Suites Chester by IHG
2 Bryle Place Chester NY
Free Cancellation
$125 nightly
The price is $148 total per night
$148 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's an indoor pool on site, and a 24-hour front desk and express check-out are also provided.
Pool
Breakfast included
Sleep Inn & Suites Monroe - Woodbury
1 Sleep Way Monroe NY
Free Cancellation
$80 nightly
The price is $90 total per night
$90 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Parking included
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Free Cancellation
$104 nightly
The price is $123 total per night
$123 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
This hotel features an indoor pool and a 24-hour 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
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
915 Union Ave New Windsor NY
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $114 total per night
$114 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Free self parking, a computer station, and luggage storage are also offered.
Pool
Pet friendly
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.
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Frequently asked questions
Where to stay in Orange County: Best areas for travelers
- Newburgh: If your ideal escape includes being close to nature, this destination will tick your boxes. Soak up the views at Bear Mountain State Park, then pay a visit to Bear Mountain State Park. Savor the fresh air of Algonquin Park and Sterling Forest State Park if you still have time. Nature buffs will also enjoy Arrow Park Lake and Lodge and Chadwick Lake Park. Some favorite hotels here are the Windsor Motel, The Inn And Spa At Beacon and the Ramada by Wyndham Newburgh/West Point.
- Town of Highlands: When it comes to putting together a Town of Highlands package, you're in the driver's seat. That means you can stay at the FairBridge Inn & Suites at West Point, the Holiday Inn Express West Point or anywhere else that appeals. During your stay, make sure to swing by West Point Golf Course.
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