Middletown Vacations from $232

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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
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
7.6/10 Good! (464 reviews)
It was quiet but smell of cigarettes even though it’s supposed to be non smoking. The carpets were filthy. Will not stay here again

Reviewed on Jul 1, 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
per person
Sep 28 - Oct 4
found 8 hours ago
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
5.4/10 (1,006 reviews)
It was cheaper than others. So my wife booked it online . Heard later from locals a little sketchy safety wise. My room was fine. Breakfast was granola bars and coffee. Hardly a brea fast. Would I stay again ? I would check into others.

Reviewed on Jul 3, 2025

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Sep 28 - Oct 4
found 8 hours ago
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
5.8/10 (1,008 reviews)
Beds were very comfortable. Staff was nice and helpful. Quiet place. Could offer more for breakfast.

Reviewed on Jul 8, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Newburgh (SWF)
9.4/10 Exceptional! (742 reviews)
I loved this hotel!!! The staff, the hotel itself, the location, everything. We will for sure stay here again

Reviewed on Jul 11, 2025

Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
6.4/10 (1,002 reviews)
Great front desk presentation by the team.

Reviewed on Jul 7, 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

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

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
$110 nightly
The price is $130 total per night from Aug 3 to Aug 4
$130 total
Aug 3 - Aug 4
Total includes taxes and fees
9.2/10 Wonderful! (743 reviews)
"Overall had a nice stay"

Reviewed on Jul 8, 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 refundableReserve now, pay when you stay
$99 nightly
The price is $116 total per night from Jul 27 to Jul 28
$116 total
Jul 27 - Jul 28
Total includes taxes and fees
8.4/10 Very Good! (1,003 reviews)
"The staff is always pleasant and the rooms are clean."

Reviewed on Jul 8, 2025

Sleep Inn & Suites Middletown - Goshen
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
3 out of 5
24 Crystal Run Xing, Middletown, NY
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Jul 27 to Jul 28
$109 total
Jul 27 - Jul 28
Total includes taxes and fees
8.4/10 Very Good! (915 reviews)
"Fast check in, clean facilities"

Reviewed on Jul 8, 2025

Courtyard by Marriott Middletown Goshen
See all 1,437 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 $232 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.