Middletown Vacation Packages

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Your Middletown Vacation

Our Middletown vacation packages allow you to create your own adventure. Tailor your journey to your needs and interests and make the most of your time in this fabulous city. Orange County Fair Speedway, Galleria at Crystal Run and Orange County Fairgrounds are just a few of the many sights you'll want to see during your trip to Middletown. Your ultimate Middletown vacation is just clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored to suit your travel style.

Top Middletown Vacation 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
Sep 26 - Sep 30
found 12 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Newburgh (SWF)
5.4/10 (1,006 reviews)
It was cheaper than others. So my wife booked it online . Heard later from locals a little sketchy safety wise. My room was fine. Breakfast was granola bars and coffee. Hardly a brea fast. Would I stay again ? I would check into others.

Reviewed on Jul. 3, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
8.2/10 Very Good! (654 reviews)
This is my 3rd hotel in my NY trip so was the best one .

Reviewed on Jul. 2, 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Aug 13 - Aug 20
found 10 hours ago
Roundtrip flight included
Ottawa (YOW) to Newburgh (SWF)
7.6/10 Good! (464 reviews)
It was quiet but smell of cigarettes even though it’s supposed to be non smoking. The carpets were filthy. Will not stay here again

Reviewed on Jul. 1, 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
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
8.4/10 Very Good! (1,004 reviews)
We'll be back. Best value rooms.

Reviewed on Jul. 13, 2025

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Sep 26 - Sep 30
found 12 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Newburgh (SWF)
5.8/10 (1,008 reviews)
Beds were very comfortable. Staff was nice and helpful. Quiet place. Could offer more for breakfast.

Reviewed on Jul. 8, 2025

Ready to book your vacation to Middletown?

 

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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 CA $150 per night from Aug 3 to Aug 4
CA $150
CA $177 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (747 reviews)
Comfortable, clean and convenient
"The manager, as well as the other customer service per person at the front desk or both amazingly professional and helpful"

Reviewed on Jul. 13, 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 CA $133 per night from Jul 27 to Jul 28
CA $133
CA $157 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"Everything was great other then the private pool lessons. The instructor was very rude with my son and with the other children. It was uncomfortable"

Reviewed on Jul. 11, 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 CA $127 per night from Jul 27 to Jul 28
CA $127
CA $150 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (918 reviews)
"The hotel was neat and clean. We had a great stay!"

Reviewed on Jul. 10, 2025

Courtyard by Marriott Middletown Goshen
See all 1,446 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Middletown

Orange County Fair Speedway

Catch an event at Orange County Fair Speedway during your trip to Mechanicstown. Discover the area's festivals and churches.

Orange County Fair Speedway

Frequently asked questions

How much does a Middletown vacation package cost?
You can snap up a vacation package to this top destination from CA $636 on Expedia. However, how much your vacation to Middletown costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Middletown?
December, January and February are great times to look for cheap Middletown vacation packages. Travelling in less busy periods means you can usually find reduced prices on flights and hotels.
How many days is enough for Middletown?
We'd recommend booking a Middletown vacation for a minimum of 2 days. This gives you enough time to tick off popular sights such as Galleria at Crystal Run and Harness Racing Museum and Hall of Fame, and also explore neighbourhoods like Scotchtown and Mechanicstown. You could even fit in a day trip from Middletown.
Is it worth booking a vacation package to Middletown?
It's easy to see why a Middletown vacation is on the must-do list of many travellers. Popular attractions like Orange County Fair Speedway are just the start of things to see and do here.
How to find the best Middletown package deals?
Finding a cheap Middletown package deal is easy with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most affordable Middletown package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Middletown vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations individually. Better still, you can personalize your Middletown trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Middletown?
Land fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Middletown break.
How to plan a trip to Middletown?

  1. Choose your travel dates: What you plan to do in Middletown and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: On top of the price of your hotel, you should consider other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that could arise during your trip to Middletown.
  3. Decide your trip length: Consider how much time you want to spend exploring Middletown. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your accommodations and airfare: After you've nailed down your dates and duration, lock in the ideal Middletown vacation package for you.

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