Middletown Holidays

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Top Flight + Hotel Deals in Middletown

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 Oct - 29 Oct
found 23 hours ago
Return direct flight included
Dublin (DUB) to Newburgh (SWF)
7.6/10 Good! (464 reviews)
Good pricing for the nice quality rooms

Reviewed on 27 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
25 Oct - 29 Oct
found 23 hours ago
Return direct flight included
Dublin (DUB) to Newburgh (SWF)
8.4/10 Very Good! (1,004 reviews)
The ad on Expedia said, "Breakfast included," except breakfast was a bag of trail mix and 2 granola bars. At 8:30 or 9am, I went to get just a little more coffee but it was all gone. Otherwise, everything was fine.

Reviewed on 28 Jul 2025

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 refundableReserve now, pay when you stay
The price is €99 per night from 24 Aug to 25 Aug
€99
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (1,012 reviews)
Rssb
"The staff was super friendly and the place was nice and clean. Comfortable bed and updated bathroom."

Reviewed on 30 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 €103 per night from 10 Aug to 11 Aug
€103
10 Aug - 11 Aug
includes taxes & fees
8.4/10 Very Good! (936 reviews)
"Very clean and friendly staff the breakfast was good but a long wait since it was only 1 staff"

Reviewed on 29 Jul 2025

Courtyard by Marriott 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 €122 per night from 3 Aug to 4 Aug
€122
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (771 reviews)
"Place was great have stayed here many times."

Reviewed on 30 Jul 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
See all 1,435 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.

Frequently asked questions

How much does a Middletown holiday package cost?
You can grab a holiday package to this destination from €567 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.