Middletown Vacations from $230

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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 $272, price is now $230 per person
$230
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
7.4/10 Good! (557 reviews)
Room was very clean but a little worn. Bed and linens were comfortable. Bathroom was clean. Very quiet. Staff were very welcoming, polite and accommodating.

Reviewed on Oct 5, 2025

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
Price was $332, price is now $283 per person
$283
per person
Nov 8 - Nov 11
found 19 hours ago
Roundtrip flight included
Miami (MIA) to Newburgh (SWF)
8.6/10 Excellent! (987 reviews)
Always clean and welcoming with a very friendly staff. We stay every year for the location close to Apple picking, farms and wineries as well as restaurants you can easily walk to.

Reviewed on Sep 25, 2025

The Lagrange Inn & Extended Stay

The Lagrange Inn & Extended Stay

2 out of 5
Price was $337, price is now $290 per person
$290
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
9.6/10 Exceptional! (9 reviews)
Love the studio room having everything we needed. Room recently renovated. Nice and cleaned

Reviewed on Sep 8, 2025

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
Price was $524, price is now $453 per person
$453
per person
Dec 19 - Dec 22
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
5.8/10 (1,004 reviews)
Very convenient to the New York thruway. Plenty of restaurants around.

Reviewed on Oct 4, 2025

Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
Price was $500, price is now $436 per person
$436
per person
Dec 19 - Dec 22
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
6.2/10 (1,003 reviews)
The employees were very nice. There were people who lived there, and they treated them like family. It could have been cleaner, I had to change rooms due to animal hair balls on the carpet, but nothing really bad. It's in a great area and was convenient for my travel purposes.

Reviewed on Sep 4, 2025

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Discover the most popular places to visit in Middletown

Orange County Fair Speedway

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

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

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

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
$101 nightly
The price is $119 total per night from Nov 9 to Nov 10
$119 total
Nov 9 - Nov 10
Total with taxes and fees
8.4/10 Very Good! (1,012 reviews)
"It was pretty quiet. The internet wasn't bad. Staff was the best. Very helpful."

Reviewed on Oct 7, 2025

Sleep Inn & Suites Middletown - Goshen
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
$117 nightly
The price is $139 total per night from Nov 3 to Nov 4
$139 total
Nov 3 - Nov 4
Total with taxes and fees
9.2/10 Wonderful! (855 reviews)
"I didn’t use"

Reviewed on Oct 6, 2025

La Quinta Inn & Suites by Wyndham 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
$97 nightly
The price is $114 total per night from Nov 9 to Nov 10
$114 total
Nov 9 - Nov 10
Total with taxes and fees
8.4/10 Very Good! (994 reviews)
"Ryyyfgyu"

Reviewed on Sep 25, 2025

Courtyard by Marriott Middletown Goshen
See all 1,436 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.

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 $230 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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Explore a world of travel with Expedia

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