Middletown Vacations from $233

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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.
Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

2.5 out of 5
Price was $269, price is now $233 per person
$233
per person
Feb 13 - Feb 16
found 20 hours ago
Roundtrip flight included
Miami (MIA) to Newburgh (SWF)
8.8/10 Excellent! (786 reviews)
This is our 2nd stay at a Holiday Inn Express in the last month and . again it is "ok". Clean, friendly staff, has the basics

Reviewed on Dec 22, 2025

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
Price was $428, price is now $344 per person
$344
per person
Jan 29 - Feb 2
found 20 hours ago
Roundtrip flight included
Miami (MIA) to Newburgh (SWF)
9.4/10 Exceptional! (906 reviews)
The room is very spacious and clean, plus the young woman that checked me in was personable and professional.

Reviewed on Dec 25, 2025

Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG

2.5 out of 5
Price was $418, price is now $351 per person
$351
per person
Feb 13 - Feb 16
found 20 hours ago
Roundtrip flight included
Miami (MIA) to Newburgh (SWF)
8.8/10 Excellent! (31 reviews)
Staff was. Excellent

Reviewed on Oct 14, 2025

Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG

2.5 out of 5
Price was $363, price is now $307 per person
$307
per person
Feb 13 - Feb 16
found 20 hours ago
Roundtrip flight included
Miami (MIA) to Newburgh (SWF)
8.8/10 Excellent! (695 reviews)
Great property right off the highway. Clean comfortable rooms, free breakfast that was pretty good. Nice staff at check-in. Tons of parking and a great basic hotel

Reviewed on Oct 13, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $318, price is now $286 per person
$286
per person
Feb 7 - Feb 9
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
8.2/10 Very Good! (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

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 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

Paramount Theatre

3.5/5(28 reviews)

You can enjoy a show at Paramount Theatre on your trip to Middletown. While in this family-friendly area, find time to visit its shops.

Paramount Theatre

Middletown Hotel Deals

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
$104 nightly
The price is $123 total per night from Jan 18 to Jan 19
$123 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
Wonderful stay rate’s very reasonable room very clean and quiet. Staff was very inviting and helpful. Looking forward to staying again went in the Middletown New York area

Reviewed on Dec 22, 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
$72 nightly
The price is $85 total per night from Jan 4 to Jan 5
$85 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
Friendly staff. Room was tidy and clean. Breakfast area was clean & organized. The only issue was that the thermostat wasn't working, and front desk said they will check on that when we check out.

Reviewed on Dec 26, 2025

Hampton Inn by Hilton Middletown
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
$97 nightly
The price is $114 total per night from Jan 11 to Jan 12
$114 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
Hotel was clean and in good condition. Convenient location. On;y provided one regular and one decaf coffee pouch even though two people in room. Did not have staff in breakfast area to take order. Had to have front desk call out to public area. Annoying to have to wait for person to take order at ...

Reviewed on Dec 21, 2025

Courtyard by Marriott Middletown Goshen
See all 1,483 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 $233 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.