Deals on vacations and trips to Middletown

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Middletown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 1
found 17 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Save 100% on your flight
per person
Sep 30 - Oct 4
found 2 hours ago
Roundtrip flight included
Houston (HOU) 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.
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Save 100% on your flight
per person
Nov 6 - Nov 9
found 21 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

2 out of 5
per person
Oct 29 - Nov 1
found 17 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
Caldwell House Bed & Breakfast

Caldwell House Bed & Breakfast

3 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 22 hours ago
Roundtrip flight included
Charlotte (CLT) to Newburgh (SWF)
This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Free full breakfast is served. A garden, a lobby fireplace, and a library are also on offer.

Top Middletown hotels deals

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
$122 nightly
The price is $144 total per night
$144 total
Aug 25 - Aug 26
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

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6, Middletown, NY
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $120 total per night
$120 total
Sep 2 - Sep 3
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

Courtyard by Marriott Middletown Goshen

3 out of 5
24 Crystal Run Xing, Middletown, NY
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $119 total per night
$119 total
Aug 24 - Aug 25
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
Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
563 Route 211 E, I-84 Exit 4W Rt 17 Exit 120, Middletown, NY
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $85 total per night
$85 total
Sep 7 - Sep 8
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.
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 out of 5
20 Crystal Run Crossing, Middletown, NY
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $117 total per night
$117 total
Aug 28 - Aug 29
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
Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown

3 out of 5
600 Route 211 East, Middletown, NY
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $167 total per night
$167 total
Sep 7 - Sep 8
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
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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 Fair Speedway

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.

Orange County Fairgrounds

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.

Galleria at Crystal Run

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 $189. 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.

Photos of local treasures

Browse Middletown vacation photos for more inspiration

Photo by Vincent Ramundo
Photo by Vincent Ramundo