Middletown Holidays

Book a Hotel + Flight or Car together to unlock savings

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 2.392.129 ₫ per night from 27 Jul to 28 Jul
2.392.129 ₫
2.825.702 ₫ total
27 Jul - 28 Jul
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"Easily accessible to visitors from out of town."

Reviewed on 22 Jun 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 2.417.702 ₫ per night from 6 Jul to 7 Jul
2.417.702 ₫
2.855.910 ₫ total
6 Jul - 7 Jul
includes taxes & fees
8.4/10 Very Good! (910 reviews)
"The pool is pretty small, but perfect for little kids. The hotel does have a few restaurants within walking distance, which was handy. Friendly and clean stay. The pull out couch was a bit disappointing. It was just a tiny bit larger than a twin."

Reviewed on 26 Jun 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 2.750.413 ₫ per night from 1 Jul to 2 Jul
2.750.413 ₫
3.248.925 ₫ total
1 Jul - 2 Jul
includes taxes & fees
9.2/10 Wonderful! (730 reviews)
"Close to shopping and lots of dinner options. Pool was great. Waffles were awesome"

Reviewed on 26 Jun 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
See all 1,428 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 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.

Popular places to visit

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

Paramount Theatre

You can enjoy a show at Paramount Theatre on your trip to Middletown. While in this family-friendly area, find time to visit its shops.

Paramount Theatre

Touro College of Osteopathic Medicine

If Touro College of Osteopathic Medicine is what brings you to town, hopefully you'll have a chance to explore more of Middletown.

Touro College of Osteopathic Medicine