Middletown Holidays
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Middletown Holiday
Our pick of the best Middletown Hotel Deals
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
NZ$213
8 Sept - 9 Sept
includes taxes & fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
551 Route 211 E Middletown NY
Fully refundableReserve now, pay when you stay
NZ$256
23 Aug - 24 Aug
includes taxes & fees
Courtyard by Marriott Middletown Goshen
24 Crystal Run Xing Middletown NY
Fully refundableReserve now, pay when you stay
NZ$203
8 Sept - 9 Sept
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 12 Aug 2026
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
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.
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.
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.
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.
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.
Paramount Theatre
7.8/10 (96 reviews)
This 1929 theatre 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.
Orange County Community College
Enjoy the student vibe at Orange County Community College during your stay in Middletown. While in this family-friendly area, you can savour the top-notch restaurants.
Frequently asked questions
How much does a Middletown holiday package cost?
You can grab a holiday package to this destination on Expedia. But how much your holiday 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 holiday packages and you could score some excellent off-season deals.
How many days is enough for Middletown?
Middletown holidays 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 neighbourhoods 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 holiday package to Middletown?
Middletown has everything you need for an unforgettable getaway. Get your Middletown holiday 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 holiday as a package?
You can enjoy significant savings on your next Middletown retreat by booking a personalised holiday 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 holiday package to Middletown?
If you've got your Middletown holiday 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?
- 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.
- Work out your budget: Ensure you have enough money to cover everything from food and transportation to activities and flights. Your accommodation will probably be the biggest expense during your trip to Middletown.
- 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.
- Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose a Middletown holiday 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.
