Middletown Holidays from AU$3,150

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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.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was AU$3,315, price is now AU$3,150 per person
AU$3,150
per person
6 Oct - 11 Oct
found 11 hours ago
Return flight included
Melbourne (AVV) to Newburgh (SWF)
7.4/10 Good! (502 reviews)
Had a good time there

Reviewed on 18 Aug. 2025

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

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

2 out of 5
Price was AU$3,377, price is now AU$3,377 per person
AU$3,377
per person
6 Oct - 11 Oct
found 11 hours ago
Return flight included
Melbourne (AVV) to Newburgh (SWF)
8.4/10 Very Good! (1,006 reviews)
This is the second time we have stayed here. The facilities are clean, the room was clean, and the staff was great. Definitely a great place to stay. So you next time!

Reviewed on 19 Aug. 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

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
The price is AU$216 per night from 25 Aug to 26 Aug
AU$216
25 Aug - 26 Aug
includes taxes & fees
9.2/10 Wonderful! (790 reviews)
I love this place
"I had another wonderful stay! The front desk staff were absolutely amazing—friendly, helpful, and quick to accommodate all of our needs with no questions asked. The room was spotless and very comfortable, which I’ve come to expect from this hotel. I’ve stayed here more than ten times now, and each ..."

Reviewed on 19 Aug. 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 AU$186 per night from 2 Sept to 3 Sept
AU$186
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,019 reviews)
"Service/staff was nice. Hotel room was clean and adequate."

Reviewed on 18 Aug. 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
The price is AU$185 per night from 24 Aug to 25 Aug
AU$185
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (958 reviews)
Marriott upstate NY
"Great place. I would say a 9.5 out of 10. Breakfast was great, just a really long wait. Lots of guests…weddings. Comfortable, safe, clean, priced competitively"

Reviewed on 17 Aug. 2025

Courtyard by Marriott Middletown Goshen
See all 1,422 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$3,150 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.

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