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

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
The price is £108 per night from 2 Aug to 3 Aug
£108
2 Aug - 3 Aug
includes taxes & fees
8.8/10 Excellent! (1,070 reviews)
"The front desk staff was wonderful. Andrea (I think that was her name) was outstanding"

Reviewed on 7 Jul 2026

Sleep Inn & Suites Middletown - Goshen
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 £109 per night from 26 Jul to 27 Jul
£109
26 Jul - 27 Jul
includes taxes & fees
9.4/10 Exceptional! (1,007 reviews)
"the breakfast was great the staff is wonderful the rooms are nice and clean stay here all the time when we go to middle town even my fur baby loves then the pool and hot tub are nice and clean excellent hotel."

Reviewed on 7 Jul 2026

La Quinta Inn & Suites by Wyndham 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 £108 per night from 12 Jul to 13 Jul
£108
12 Jul - 13 Jul
includes taxes & fees
8.4/10 Very good! (1,001 reviews)
"Accommodated an early check in for our wedding party which was wonderful"

Reviewed on 5 Jul 2026

Courtyard by Marriott Middletown Goshen
See all 1,510 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.
All Inclusive Holidays
All Inclusive Holidays
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Family Friendly Holidays

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.
See properties

What to do in Middletown

LEGOLAND New York Resort Admission Ticket

LEGOLAND New York Resort Admission Ticket

£39
per traveller
84% of travellers recommend
LEGOLAND New York Resort Admission Ticket
See all activities in Middletown

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.