Middletown Holidays from AU$3,087

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Your Middletown Holiday

The adventure-packed city of Middletown is calling. Immerse yourself in everything it has to offer with a Middletown holiday package that's customised to you. If sightseeing is on the agenda during your trip to Middletown, stop by popular attractions like Orange County Fair Speedway, Orange County Fairgrounds and Galleria at Crystal Run. Expedia will help you escape your daily routine. Tailor your holiday to Middletown to match your travel style, whatever that may look like.

The Latest Middletown Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
per person
13 Apr - 18 Apr
found 1 day ago
Return direct flight included
Sydney (SYD) to Newburgh (SWF)
5.4/10 (1,004 reviews)
Overall, below average but still descent place to stay. Thank you

Reviewed on 23 Feb. 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
13 Apr - 18 Apr
found 1 day ago
Return direct flight included
Sydney (SYD) to Newburgh (SWF)
8.2/10 Very Good! (611 reviews)
Everything great.. except pool area could use upgrade.

Reviewed on 10 Mar. 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
13 Apr - 18 Apr
found 1 day ago
Return direct flight included
Sydney (SYD) to Newburgh (SWF)
8.4/10 Very Good! (1,005 reviews)
The room was fine, beds were quite comfy. But, the cleaning staff was ridiculously loud very early in the morning, a horn kept beeping all night outside our room, the remote didn’t work, and the pool wasn’t open.

Reviewed on 9 Mar. 2025

Middletown Holiday

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, Paramount Theatre and Castle Fun Centre

Our pick of the best Middletown Hotel Deals

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 AU$156 per night from 17 Mar to 18 Mar
AU$156
includes taxes & fees
17 Mar - 18 Mar
8.6/10 Excellent! (1,014 reviews)
"Very affordable hotel with many amenities"

Reviewed on 9 Mar. 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 AU$174 per night from 16 Mar to 17 Mar
AU$174
includes taxes & fees
16 Mar - 17 Mar
8.4/10 Very Good! (842 reviews)
"Nice hotel. Was clean"

Reviewed on 8 Mar. 2025

Courtyard by Marriott Middletown Goshen
Tru by Hilton Middletown
Tru by Hilton Middletown
2.5 out of 5
41 Dunning Road, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 23 Mar to 24 Mar
AU$174
includes taxes & fees
23 Mar - 24 Mar
8.4/10 Very Good! (885 reviews)
"Modern up to date"

Reviewed on 8 Mar. 2025

Tru by Hilton Middletown
See all 1,392 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

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Middletown holiday package cost?
You can grab a holiday package to this destination from AU$3,087 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?

  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 accommodation 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 holiday package that brings all your bookings together.

Discover the most popular places to visit in Middletown

Galleria at Crystal Run

During your visit to Middletown, you can do some window-shopping at Galleria at Crystal Run. While in this family-friendly area, you can savour the top-notch restaurants.

Galleria at Crystal Run
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.