Middletown Vacations from $268

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Your Middletown Vacation

Our Middletown vacation packages allow you to create your own adventure. Tailor your journey to your needs and interests and make the most of your time in this fabulous city. Orange County Fair Speedway, Galleria at Crystal Run and Orange County Fairgrounds are just a few of the many sights you'll want to see during your trip to Middletown. Your ultimate Middletown vacation is just clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored to suit your travel style.

The Latest Middletown 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
Price was $356, price is now $268 per person
$268
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Miami (MIA) to Newburgh (SWF)
14.4/10 Exceptional! (679 reviews)
Yes, every thing was clean. Staff was very friendly. My only complaint was , that a handicap room should have a raised toilet in those rooms.

Reviewed on Oct 31, 2025

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
Price was $337, price is now $272 per person
$272
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Miami (MIA) to Newburgh (SWF)
17.2/10 Exceptional! (1,000 reviews)
I always enjoy my stay here when I come to visit family!

Reviewed on Nov 25, 2025

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
Price was $488, price is now $413 per person
$413
per person
Dec 26 - Dec 30
found 10 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Newburgh (SWF)
10.8/10 Exceptional! (1,002 reviews)
Leave before breakfast, needs some updates

Reviewed on Nov 17, 2025

Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown

2 out of 5
Price was $629, price is now $536 per person
$536
per person
Dec 26 - Dec 30
found 10 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Newburgh (SWF)
14/10 Exceptional! (1,000 reviews)
Didn't have breakfast

Reviewed on Oct 27, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $457, price is now $392 per person
$392
per person
Feb 12 - Feb 15
found 10 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
16.4/10 Exceptional! (691 reviews)
Great location and it felt pretty safe overall. The only downside was that the room didn’t have proper humidity ventilation, and the hallway AC made it cold, so we had to use the heater to balance the temperature. Other than that, the staff was super friendly, and the property was very well maintained.

Reviewed on Oct 30, 2025

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Discover the most popular places to visit in Middletown

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

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

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

Middletown Hotel 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
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $136 total per night from Dec 17 to Dec 18
$136 total
Dec 17 - Dec 18
Total with taxes and fees
9.2/10 Wonderful! (918 reviews)
Did not like the eggs

Reviewed on Nov 23, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
$101 nightly
The price is $119 total per night from Dec 15 to Dec 16
$119 total
Dec 15 - Dec 16
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
The breakfast had a good variety. The staff was always very pleasant. The room was neat and clean.

Reviewed on Nov 18, 2025

Sleep Inn & Suites Middletown - Goshen
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 out of 5
20 Crystal Run Crossing Middletown NY
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $94 total per night from Dec 2 to Dec 3
$94 total
Dec 2 - Dec 3
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
Breakfast was very good, room was clean, however no information about check out, simlply no information about anyfhing

Reviewed on Nov 15, 2025

Hampton Inn by Hilton Middletown
See all 1,460 properties in Middletown
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.

Find the Best Middletown Vacation Packages

Middletown Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
27,800
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Warwick Valley Winery and Distillery, Castle Fun Center and Paramount Theatre

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Frequently asked questions

How much does a Middletown vacation package cost?
You can grab a vacation package to this destination from $268 on Expedia. But how much your vacation to Middletown costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Middletown?
You can typically find reduced prices and greater availability in November, December and January. Browse our cheap Middletown vacation packages and you could land some great off-season discounts.
How many days is enough for Middletown?
We'd recommend booking a Middletown vacation for a minimum of 2 days. This will give you time to check off top attractions including Orange County Fair Speedway and Orange County Fairgrounds, and check out neighborhoods like Scotchtown and Mechanicstown. You might even be able to fit in a day trip (or two) beyond Middletown.
Is it worth booking a vacation package to Middletown?
Middletown offers everything you need for a wonderful getaway. Begin your Middletown vacation on a high note by checking out popular attractions like Orange County Fair Speedway.
How to find the best Middletown package deals?
Start your search for a Middletown package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Middletown package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Middletown adventure underway.
Is it cheaper to book a Middletown vacation as a package?
You can enjoy significant savings on your next Middletown retreat by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Middletown?
If you've got your Middletown vacation dates confirmed, book early to snap up some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Middletown?

  1. Choose when to travel: Check your diary and get packing. Your favorite season and the activities on offer will also help you decide when to escape to Middletown.
  2. Budget wisely: In addition to the price of your hotel, you should factor in other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Middletown.
  3. Use our trip planning tool to explore Middletown: Research every part of your trip to Middletown with this handy planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Decide how long to go away for: Now that you know more about Middletown, you can figure out the ideal length of your vacation. Create a rough itinerary and give yourself enough time to get through everything on your must-do list.
  5. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Middletown vacation package that brings all your bookings together.
  6. Book activities and experiences in advance: Whether it's entrance to a big attraction or a day trip in nature, you won't have to worry about missing out on the best Middletown has to offer. Find all the fun things to do in Middletown with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Middletown vacation packages?
Your Middletown trip is meant to be a relaxing escape from your daily routine, not a reason for money worries. So to allow you extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.