Middletown Vacation Packages 2025 from $323

Middletown flight + hotel vacation packages

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

Super 8 by Wyndham Montgomery Maybrook

per person

Jul 23 - Jul 26

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Newburgh (SWF)

This motel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free buffet breakfast each morning. A safe deposit box is provided and the front desk is staffed around-the-clock.

YO1 Longevity & Health Resorts, Catskills

Save 100% on your flight

per person

Jul 10 - Jul 13

found 20 hours ago

Roundtrip flight included

Chicago (ORD) to Newburgh (SWF)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the indoor pool and perks like free self parking.

The Crossroads Hotel, Newburgh

per person

Aug 17 - Aug 21

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Newburgh (SWF)

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.

The Yarra

per person

Jul 10 - Jul 13

found 20 hours ago

Roundtrip flight included

Chicago (ORD) to Newburgh (SWF)

A restaurant, free self parking, and a garden are among this inn's amenities. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A communal living room, a picnic area, and express check-out are also on offer.

La Quinta Inn & Suites by Wyndham Middletown-Goshen

per person

Jul 10 - Jul 13

found 20 hours ago

Roundtrip flight included

Chicago (ORD) to Newburgh (SWF)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Top Middletown hotels deals

Sleep Inn & Suites Middletown - Goshen

3491 Route 6, Middletown, NY

Free Cancellation

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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

Super 8 by Wyndham Middletown

563 Route 211 E, I-84 Exit 4W Rt 17 Exit 120, Middletown, NY

Free Cancellation

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This motel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. Luggage storage and a safe deposit box are also provided.

Breakfast included

Parking included

La Quinta Inn & Suites by Wyndham Middletown-Goshen

551 Route 211 E, Middletown, NY

Free Cancellation

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This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Hampton Inn by Hilton Middletown

20 Crystal Run Crossing, Middletown, NY

Free Cancellation

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This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Courtyard by Marriott Middletown Goshen

24 Crystal Run Xing, Middletown, NY

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A 24-hour business center, express check-out, and luggage storage are also on offer.

Pool

Pet friendly

Microtel Inn & Suites by Wyndham Middletown

19 Crystal Run Crossing, Middletown, NY

Free Cancellation

Reserve now, pay when you stay

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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 computer station, dry cleaning, and luggage storage are also on offer.

Breakfast included

Pet friendly

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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.

Popular places to visit

Orange County Fair Speedway

4/5(5 reviews)

Catch an event at Orange County Fair Speedway during your trip to Mechanicstown. Discover the area's festivals and churches.

Orange County Fairgrounds

4.5/5(4 reviews)

Enjoy an outing to Orange County Fairgrounds during your stay in Mechanicstown. Discover the area's festivals and churches.

Galleria at Crystal Run

4/5(20 reviews)

During your visit to Middletown, you can search for that perfect souvenir at Galleria at Crystal Run. While in this family-friendly area, you can savor the top-notch restaurants.

Frequently asked questions

How much are vacation packages to Middletown?

Vacation packages, which include hotels and flights in Middletown, are priced from as little as $323. Turn your travel dreams into reality and lock in your trip with Travelocity today.

How long should my Middletown vacation be?

Around 2 nights is what many visitors book for their Middletown vacation. That’s a great guide, but there’s plenty more to explore if you allow yourself a few extra days.

Where can I get the best vacation package deals for Middletown?

It’s difficult to beat Travelocity when it comes to piecing together your Middletown package deal. There are at least 400 airlines and 1,000,000 properties around the world to select from. Plan your escape now and get ready to cross another exciting destination off your must-visit list.

Why should I book my Middletown vacation package with Travelocity?

Savings, support and a stress-free booking are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to round-the-clock support. With the Travelocity Price Match Guarantee, you know you’ll always get the best deal available.

Will I save money on my Middletown car rental if I book it with a hotel or flight?

With a Middletown vacation package, you can bundle your flight, car and hotel bookings and save loads. If you’re in the mood to uncover the best of this fantastic destination, why not make a beeline for Times Square? This top sight is 55 mi from Middletown. With a rental car, you’ll be there in no time.

Which airport is best for Middletown?

Liberty Intl. Airport (EWR) is 55 mi from the downtown area and is the starting point for many unforgettable experiences. Alternatively, LaGuardia Airport (LGA) is 55 mi away from central Middletown and Stewart Intl. Airport (SWF) is 18 mi away from central Middletown.

What is there to do in Middletown?

While veering off the tourist trail is no doubt rewarding, you shouldn’t ignore the popular sights that make a place famous. Orange County Fair Speedway and Orange County Fairgrounds are just two of them in Middletown.

Where should I stay when visiting Middletown?

If you’re looking for someplace comfortable to lay your head, take a look at the Holiday Inn Express & Suites Middletown - Goshen, an IHG Hotel. It’s the top pick for many travelers.