Middletown Holidays
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Your Middletown Holiday
Our Middletown holiday 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 holiday is just clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored to suit your travel style.
Middletown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Stewart Intl. Airport (SWF) |
Population | 27,800 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Warwick Valley Winery and Distillery, Castle Fun Centre and Harness Racing Museum and Hall of Fame |
Top hotels in Middletown
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
£96
8 Sept - 9 Sept
includes taxes & fees
8.8/10 Excellent! (1,122 reviews)
"Great location. Breakfast was good with plenty of tasty options"
Reviewed on 8 Aug 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
551 Route 211 E Middletown NY
Fully refundableReserve now, pay when you stay
£108
31 Aug - 1 Sept
includes taxes & fees
Courtyard by Marriott Middletown Goshen
24 Crystal Run Xing Middletown NY
Fully refundableReserve now, pay when you stay
£92
23 Aug - 24 Aug
includes taxes & fees
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.
What to do in Middletown
LEGOLAND New York Resort Admission Ticket
£38
per traveller
84% of travellers recommend
Frequently asked questions
Why should I book my Middletown holiday with Expedia?
Expedia has you covered for every aspect of your next Middletown getaway. You'll always get the best deals, but when you bundle your accommodation, flights and/or car hire into a holiday package, you'll get even bigger savings. Want to really make the most of your escape? Add a few exciting tours and activities to your package. Expedia offers flexible cancellation policies on most bookings, so you won't need to worry if your travel plans change. Visit our Customer Service Portal link to find out more.
When is the best time of year to holiday in Middletown?
If you love the excitement that comes with peak season, visit Middletown in March, July and August. Travelling during the quieter months of November, December and January will help you avoid the crowds. Plan your getaway to Middletown according to what type of adventure you're looking for. January is the coolest month, when average daytime temperatures are -3ºC. In July, the warmest month, you'll experience averages of 22ºC during the day.
What are the top hotels for my holiday in Middletown?
Super 8 by Wyndham Middletown and Hampton Inn by Hilton Middletown are among the best getaways in the neighbourhood of Mechanicstown. If you're thinking of staying in the Scotchtown area, check in to Home2 Suites by Hilton Middletown or Holiday Inn Express & Suites Middletown - Goshen, an IHG Hotel.
How do I get a cheap holiday to Middletown?
Booking a flight and hotel together with Expedia won't just save valuable time — it'll save you a nice amount too. A Middletown holiday makes it simple to create the perfect trip. With more than 400 airlines around the world to pick from, finding convenient flights that suit your busy schedule will be no sweat. On top of that, we have over 321,000 properties globally to select from. Now that's choice! No matter who you are, Expedia can show you the world. Learn more about how you can save money on your next holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Middletown holiday?
There's an almost endless list of things to see and do while enjoying your holiday in Middletown. LEGOLAND® New York, Orange County Fair Speedway, Orange County Fairgrounds and Galleria at Crystal Run are just some of this city's best attractions.
What is the best area to stay in when on holiday in Middletown?
Middletown has lots of interesting places to see, like Orange County Fair Speedway. Stay somewhere nearby and make sightseeing a breeze.
Do I need a visa for my Middletown holiday?
Official government websites are the best source of information on visa requirements, application procedures and any supporting documentation. Your nationality and the reason for your visit, whether it be for holidays or business, will determine if you need a visa for Middletown. Also check that your passport is up to date and has a minimum of six months validity remaining beyond your intended return date. Finalise all your travel planning ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Middletown holiday?
First, consider the activities planned during your trip to Middletown and choose versatile pieces that you can mix and match. For fashion inspiration or information on any dress codes, browse style blogs or relevant social media accounts. Pack appropriately by checking the weather conditions in Middletown. July brings the warmest temperatures, with daytime averages of 22ºC, while January days average -3ºC, making it the coolest time of year.
What does an Expedia Middletown holiday include?
Hotels, flights and hire cars — we've got them covered. With Expedia, you can shape your Middletown package the way you like it. All you have to do is decide just what you need. Once you've made your booking, why not add extras like activities and experiences? The more you bundle, the more you save! Expedia features all kinds of properties, with the most popular in Middletown including private holiday homes and hotels. With Expedia, you'll always have the flexibility and freedom to tailor your holiday any way you want.
Does Expedia offer Book Now, Pay Later Middletown holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has worked out a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a fabulous getaway without eating away at your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Check out these flexible payment options:
- Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna offers just that! Paying in multiple instalments will make your holiday dreams come true.
- No-deposit holidays: If not paying ahead of time for your getaway makes pressing that "book now" button easier, opt for a no-deposit holiday plan from Klarna so that you can Book Now, Pay Later!
Can I choose my airline with a Middletown Expedia holiday?
Expedia offers access to more than 400 partner airlines globally, so you definitely can. Simply choose your preferred air carrier and put together the perfect Middletown trip.
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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. Flight-inclusive packages are ATOL protected.
