Middletown Vacation Packages 2026 from $560

Middletown flight + hotel vacation packages

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

Pine Brook Manor

$560

per person

May 23 - May 25

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Newburgh (SWF)

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free local cuisine breakfast each morning. A terrace and a picnic area are also provided.

YO1 Longevity & Health Resorts, Catskills

$633

per person

May 23 - May 25

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Resorts World Catskills Casino

$635

per person

May 23 - May 25

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Newburgh (SWF)

This luxury hotel features a casino, a full-service spa, and 6 restaurants. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 6 bars/lounges.

Courtyard by Marriott Newburgh Stewart Airport

$592

per person

May 23 - May 25

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Newburgh (SWF)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.

Top Middletown hotels deals

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

Free Cancellation

$108 nightly

$127 total

Mar 15 - Mar 16

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

Courtyard by Marriott Middletown Goshen

24 Crystal Run Xing Middletown NY

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$109 total

Mar 15 - Mar 16

Total with 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

$93 nightly

$109 total

Mar 19 - Mar 20

Total with 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

Tru by Hilton Middletown

41 Dunning Road Middletown NY

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$119 total

Mar 19 - Mar 20

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free English breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and free newspapers.

Breakfast included

Pet friendly

Holiday Inn Express & Suites Middletown - Goshen by IHG

20 MED PARC ROAD Middletown NY

Free Cancellation

$118 nightly

$139 total

Mar 15 - Mar 16

Total with taxes and fees

This hotel features an indoor pool and a 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

Residence Inn by Marriott Middletown Goshen

57 TOWER DRIVE Middletown NY

$188 nightly

$222 total

Mar 22 - Mar 23

Total with 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 and free internet in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Don't see what you're looking for?

See all available properties in Middletown

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.

Popular places to visit

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.

Overview of Cold Spring and Hudson Highlands State Park in Fall, New York - October 2024

Highland Lakes State Park

You can take time to visit Highland Lakes State Park during your travels to Middletown. While in this family-friendly area, you can savor the top-notch restaurants.

Lake George on a summer day, in Bolton, New York

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Middletown. 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 $560. 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.