Middletown Vacation Packages 2025/2026 from $319

Middletown flight + hotel vacation packages

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

Howard Johnson by Wyndham Newburgh/West Point

per person

Sep 11 - Sep 15

found 8 hours ago

Roundtrip flight included

Miami (MIA) to Newburgh (SWF)

This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

per person

Oct 8 - Oct 12

found 18 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Newburgh (SWF)

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.

The Crossroads Hotel, Newburgh

per person

Oct 8 - Oct 12

found 15 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) 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.

Wildflower Farms, Auberge Resorts Collection

per person

Sep 25 - Sep 27

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Newburgh (SWF)

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.

Hampton Inn & Suites Newburgh Stewart Airport

per person

Oct 10 - Oct 14

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Newburgh (SWF)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free airport shuttle. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Top Middletown hotels deals

La Quinta Inn & Suites by Wyndham Middletown-Goshen

551 Route 211 E, Middletown, NY

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$130 total

Aug 3 - Aug 4

Total includes taxes and fees

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

Sleep Inn & Suites Middletown - Goshen

3491 Route 6, Middletown, NY

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$115 total

Aug 17 - Aug 18

Total includes 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

Courtyard by Marriott Middletown Goshen

24 Crystal Run Xing, Middletown, NY

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$109 total

Jul 27 - Jul 28

Total includes taxes and fees

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

Hampton Inn by Hilton Middletown

20 Crystal Run Crossing, Middletown, NY

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$122 total

Aug 10 - Aug 11

Total includes taxes and fees

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

Super 8 by Wyndham Middletown

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

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$89 total

Jul 27 - Jul 28

Total includes taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage and a safe deposit box are also provided.

Parking included

Free WiFi

Microtel Inn & Suites by Wyndham Middletown

19 Crystal Run Crossing, Middletown, NY

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$130 total

Aug 10 - Aug 11

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 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

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

Orange County Fairgrounds

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

Galleria at Crystal Run

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 $319. 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.