Middletown Vacations

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Find the Best Middletown Vacation Packages

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
The price is NT$3,595 per night from Aug 25 to Aug 26
NT$3,595
NT$4,247 total
Aug 25 - Aug 26
includes taxes & fees
9.2/10 Wonderful! (789 reviews)
"Our room...and all areas of the Hotel were very clean and well maintained. Staff was very helpful..and friendly!"

Reviewed on 2025/8/17

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
The price is NT$3,058 per night from Sep 2 to Sep 3
NT$3,058
NT$3,613 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (1,015 reviews)
"Really nice place, new and breakfast on point! Located right off highway."

Reviewed on 2025/8/17

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
The price is NT$3,034 per night from Aug 24 to Aug 25
NT$3,034
NT$3,584 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (957 reviews)
Marriott upstate NY
"Great place. I would say a 9.5 out of 10. Breakfast was great, just a really long wait. Lots of guests…weddings. Comfortable, safe, clean, priced competitively"

Reviewed on 2025/8/17

Courtyard by Marriott Middletown Goshen
See all 1,422 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.

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

Frequently asked questions

How much does a Middletown vacation package cost?
You can grab a vacation package to this destination 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're likely to find reduced prices and better availability in December, January and February. Check out our cheap Middletown vacation packages and you could score some excellent off-season deals.
How many days is enough for Middletown?
Middletown vacations can be as short or long as you like, but to really sink your teeth into this destination, we reckon 2 days is about right. In this timeframe, you can fit in top sights like Orange County Fair Speedway and Paramount Theatre and track down some lesser-known gems. Don't skip neighborhoods such as Scotchtown and Mechanicstown either. If you plan wisely, you can even take a day trip outside of Middletown too.
Is it worth booking a vacation package to Middletown?
Middletown has everything you need for an unforgettable getaway. Get your Middletown vacation off to a flying start by exploring major 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 get away: Check your calendar and get your bags packed. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Middletown.
  2. Work out your budget: Ensure you have enough money to cover everything from food and transportation to activities and flights. Your accommodations will probably be the biggest expense during your trip to Middletown.
  3. Determine how many days away: Start by listing all the sights and activities you'd like to get to in Middletown. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose a Middletown vacation package that brings all your bookings together.

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