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A large steel bridge spanning a river, surrounded by trees and buildings.

Middletown

Vacations
Middletown

Orange County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,272, price is now CA $752 per person
CA $752
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Times Square and Broadway are located nearby.
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was CA $1,973, price is now CA $1,086 per person
CA $1,086
per person
Sep 3 - Sep 7
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Manhattan Cruise Terminal and Broadway are located nearby.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,496, price is now CA $1,434 per person
CA $1,434
per person
Sep 3 - Sep 7
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Times Square are located nearby.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,530, price is now CA $1,458 per person
CA $1,458
per person
Aug 12 - Aug 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Rockefeller Center are located nearby.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,308, price is now CA $766 per person
CA $766
per person
Aug 12 - Aug 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a steam room, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Central Park and Metropolitan Museum of Art are located nearby.

Top Orange County hotels deals

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Free cancellation
The price is CA $155 per night
CA $155
CA $183 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Orange County Community College and Paramount Theatre are located nearby.
Pool
Breakfast included
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Free cancellation
Reserve now, pay when you stay
The price is CA $199 per night
CA $199
CA $244 total
Jul 12 - Jul 13
includes taxes & fees
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Bear Mountain State Park and Monteverde at Oldstone are located nearby.
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E Middletown NY
Free cancellation
Reserve now, pay when you stay
The price is CA $176 per night
CA $176
CA $208 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.
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
The price is CA $115 per night
CA $115
CA $135 total
Jul 12 - Jul 13
includes taxes & fees
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and a nightclub. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
Parking included
Free WiFi
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

2.5 out of 5
1 Sleep Way Monroe NY
Free cancellation
The price is CA $156 per night
CA $156
CA $176 total
Aug 3 - Aug 4
includes taxes & fees
Book a stay at this business-friendly hotel in Monroe. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodbury Common Premium Outlets and Museum Village are located nearby.
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
2 Bryle Place Chester NY
Free cancellation
The price is CA $144 per night
CA $144
CA $177 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LEGOLAND® New York and Castle Fun Center are located nearby.
Pool
Breakfast included
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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 Orange County attractions

LEGOLAND® New York

9.0/10 (279 reviews)
Have a fun-filled day at LEGOLAND® New York and see why everyone loves this theme park in Goshen. Make some time to visit the cathedral while you're in the area.
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Photos of local treasures

Browse Orange County vacation photos for more inspiration

A dog sitting on a bench by a calm lake surrounded by trees.
A river valley with dense forest and a bridge.
A person sitting on a concrete bench overlooking a river and hills.
A hilly landscape with dense green forests and a clear sky.
A stone tower with a green roof and antenna, surrounded by rocky terrain and sparse trees.

Frequently asked questions

How much are vacation packages to Orange County?
You can find a great hotel + flight bundle for an affordable CA $752. With one of our Travelocity vacation packages, a getaway to Orange County has never looked so enticing! Save your time and money and then get a head start on packing those bags.
Where can I get the best vacation package deals for Orange County?
You'll find fantastic Orange County package deals with Travelocity. Pick and choose from 400 air carriers and 1,000,000 worldwide properties and turn those travel dreams into reality.
Why should I purchase my Orange County vacation package via Travelocity?
Because we believe in creating unforgettable vacation experiences. From flights and hotels to car rentals and activities, our packages make it a breeze to save. Our support team is on hand 24/7 to make sure you'll never wander alone. We also offer a Price Match Guarantee, so you can book your trip knowing you've scored the best deal possible. Find a lower price and we'll match it!
Can I save money on my Orange County car rental if I bundle it with a hotel or flight?
Combining your bookings into an Orange County vacation package will save you some serious money. Book a flight and car; a car, hotel and flight; or a hotel and car. You won't find a better way to discover the greater Orange County region than with your own set of wheels. You can also add activities and experiences to your Travelocity package.
Which airport is best for Orange County?
John F. Kennedy Intl. Airport (JFK) is an excellent option for visitors jetting into Orange County. Liberty Intl. Airport (EWR) and LaGuardia Airport (LGA) also welcome many of the flights into the region.
What is there to do in Orange County?
A diverse and attractive destination, Orange County boasts some fantastic tourist attractions. Orange County Fair Speedway and Warwick Valley Winery and Distillery are just a couple of the most popular.