Middletown Holidays

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Middletown Holiday

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 NZ$236 per night from 29 Nov to 30 Nov
NZ$236
29 Nov - 30 Nov
includes taxes & fees
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
The price is NZ$218 per night from 6 Dec to 7 Dec
NZ$218
6 Dec - 7 Dec
includes taxes & fees
8.8/10 Excellent! (1,257 reviews)
"Room was excellent service great customer service front desk breakfast was excellent highly recommended. Five stars"

Reviewed on 13 Nov 2026

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 NZ$216 per night from 6 Dec to 7 Dec
NZ$216
6 Dec - 7 Dec
includes taxes & fees
Courtyard by Marriott Middletown Goshen
See all 1,509 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.

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

Frequently asked questions

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