Middletown Holidays from £631

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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.

Top Middletown Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
25 Aug - 30 Aug
found 7 hours ago
Return flight included
London (LON) to Newburgh (SWF)
7.6/10 Good! (464 reviews)
It was quiet but smell of cigarettes even though it’s supposed to be non smoking. The carpets were filthy. Will not stay here again

Reviewed on 1 Jul 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
per person
6 Sept - 11 Sept
found 1 day ago
Return flight included
Manchester (MAN) to Newburgh (SWF)
8.4/10 Very Good! (1,004 reviews)
We'll be back. Best value rooms.

Reviewed on 13 Jul 2025

Newburgh Inn

Newburgh Inn

2 out of 5
per person
19 Sept - 22 Sept
found 16 hours ago
Return flight included
London (LON) to Newburgh (SWF)
5.2/10 (95 reviews)
There was confusion upon arrival where I was no where to be found in the system, however, the friendly hotel concierge made it work by reaching out to another hotel facility to ensure we no longer had to wait for the room I already paid for. The shower was nice, someone was already previously logged into Netflix (also nice) and we had everything we needed for the short night stay (easy to extend checkout by calling on personal phone due to no landline present).

Reviewed on 24 Dec 2024

Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG

2.5 out of 5
per person
19 Sept - 22 Sept
found 16 hours ago
Return flight included
London (LON) to Newburgh (SWF)
8.8/10 Excellent! (661 reviews)
Great property to stay at for a few nights to take my family to Lego land. Very friendly staff. Exceeded our expectations. Would stay here again in the future.

Reviewed on 1 Jul 2025

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
per person
27 Aug - 30 Aug
found 1 day ago
Return flight included
London (LON) to Newburgh (SWF)
9.2/10 Wonderful! (916 reviews)
Decent, clean, environmentally concious

Reviewed on 8 Jul 2025

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

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 £96 per night from 3 Aug to 4 Aug
£96
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (746 reviews)
"I loved this hotel!!! The staff, the hotel itself, the location, everything. We will for sure stay here again"

Reviewed on 11 Jul 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
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 £88 per night from 3 Aug to 4 Aug
£88
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (1,012 reviews)
"All staff were super friendly and helpful!"

Reviewed on 13 Jul 2025

Sleep Inn & Suites 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 £82 per night from 27 Jul to 28 Jul
£82
27 Jul - 28 Jul
includes taxes & fees
8.4/10 Very Good! (920 reviews)
"Loved it"

Reviewed on 12 Jul 2025

Courtyard by Marriott Middletown Goshen
See all 1,424 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

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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.

* 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.