Middletown Vacations

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Find the Best Middletown Vacation Packages

Middletown Hotel Deals

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY
Fully refundable
NT$3,404
NT$4,021 total
Sep 8 - Sep 9
includes taxes & fees
8.8/10 Excellent! (1,130 reviews)
"Room was clean. Check in and out was fast and easy. Only wish I would have used my choice rewards prior to booking to get the points. I forgot and points can’t be added :("

Reviewed on 2026/8/15

Sleep Inn & Suites Middletown - Goshen
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

551 Route 211 E Middletown NY
Fully refundableReserve now, pay when you stay
NT$4,065
NT$4,802 total
Aug 30 - Aug 31
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"This was a very beautiful hotel, very clean. The breakfast was amazing and the customer service was excellent. I definitely will be returning for another day in the future."

Reviewed on 2026/8/15

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

24 Crystal Run Xing Middletown NY
Fully refundableReserve now, pay when you stay
NT$3,240
NT$3,828 total
Aug 23 - Aug 24
includes taxes & fees
8.4/10 Very Good! (1,013 reviews)
"Clean. Close to food. Walked to Outback Steakhouse. Great food and great service."

Reviewed on 2026/8/12

Courtyard by Marriott Middletown Goshen
See all 1,497 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.

Stay near popular Middletown attractions

A large Ferris wheel against a sunset sky.

Orange County Fairgrounds

8.0/10 (87 reviews)
This historic fairgrounds combines a century-old county fair with thrilling dirt track racing. Enjoy carnival rides during the July fair or catch heart-pounding motorsport action at the legendary speedway.
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A lake surrounded by dense vegetation and a hill with a house in the background.

Highland Lakes State Park

8.0/10 (43 reviews)
Discover 3,115 acres of pristine wilderness with informal trails winding through forests and around lakes. Bring supplies for horseback riding, fishing, or hiking in this peaceful, undeveloped natural retreat.
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A lake with boats, docks, and trees.

Highland Lake

10.0/10 (3 reviews)
Explore 3,000 acres of pristine wilderness at this undeveloped sanctuary for outdoor enthusiasts. Hike forest trails, cast a line in serene lakes, or ride horseback with a permit through untouched nature.
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Orange County Fair Speedway

8.4/10 (119 reviews)
America's oldest continuously operating dirt track, Orange County Fair Speedway has thrilled racing fans since 1919. Experience the roar of engines and excitement of dirt track racing at this historic motorsport venue.
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Galleria at Crystal Run

8.6/10 (200 reviews)
The Galleria at Crystal Run offers over 100 stores and entertainment venues in the heart of Middletown. Explore premium retailers like Macy's or catch a film at the cinema for a complete shopping experience.
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Paramount Theatre

7.8/10 (96 reviews)
This 1929 theater boasts Carnegie Hall-like acoustics, hosting diverse performances in its intimate 1,100-seat venue. Experience cultural richness through concerts, films, or shows in this historic Middletown gem.
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Orange County Community College

Enjoy the collegiate vibe at Orange County Community College during your visit to Middletown. While in this family-friendly area, you can savor the top-notch restaurants.
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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.

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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.