Middletown Vacations from ￥206,223

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The Latest Middletown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newburgh (SWF)
8.2/10 Very Good! (644 reviews)
Always a great stay. Staff is exceptional.

Reviewed on May 29, 2025

Find the Best Middletown Vacation Packages

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
The price is ￥13,155 per night from Jul 1 to Jul 2
￥13,155
￥15,538 total
Jul 1 - Jul 2
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Very comfortable, clean room. There was even a recliner! Good breakfast compared to most hotels now."

Reviewed on Jun 18, 2025

Sleep Inn & Suites Middletown - Goshen
Super 8 by Wyndham Middletown
Super 8 by Wyndham Middletown
2.5 out of 5
563 Route 211 E, I-84 Exit 4W Rt 17 Exit 120, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is ￥10,928 per night from Jul 2 to Jul 3
￥10,928
￥12,909 total
Jul 2 - Jul 3
includes taxes & fees
6.2/10 (1,000 reviews)
"Very nice stay. Will return again."

Reviewed on Jun 16, 2025

Super 8 by Wyndham Middletown
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 ￥17,261 per night from Jun 25 to Jun 26
￥17,261
￥20,391 total
Jun 25 - Jun 26
includes taxes & fees
9.2/10 Wonderful! (719 reviews)
"Very comfortable and employees were very welcoming. The room was large and the bed comfortable."

Reviewed on Jun 16, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
See all 1,438 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.

Frequently asked questions

How much does a Middletown vacation package cost?
You can grab a vacation package to this destination from ￥206,223 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.