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 Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newburgh (SWF)
6.4/10 (1,002 reviews)
Well done all around. Good value

Reviewed on Aug. 8, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Nov 1 - Nov 3
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newburgh (SWF)
8.2/10 Very Good! (671 reviews)
Staff was friendly and attentive to any needs I may have had, I definitely would stay here again

Reviewed on Aug. 6, 2025

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
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newburgh (SWF)
5.4/10 (1,004 reviews)
Nice reasonable place to stay

Reviewed on Jul. 20, 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Sep 12 - Sep 16
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
7.4/10 Good! (502 reviews)
Comfortable place to stay

Reviewed on Aug. 7, 2025

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newburgh (SWF)
5.8/10 (1,002 reviews)
Beds were very comfortable. Staff was nice and helpful. Quiet place. Could offer more for breakfast.

Reviewed on Jul. 8, 2025

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Middletown Hotel Deals

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 $140 per night from Sep 7 to Sep 8
CA $140
CA $166 total
Sep 7 - Sep 8
includes taxes & fees
8.4/10 Very Good! (1,015 reviews)
"Breakfast items not available after 9am."

Reviewed on Aug. 11, 2025

Sleep Inn & Suites 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 CA $163 per night from Aug 25 to Aug 26
CA $163
CA $192 total
Aug 25 - Aug 26
includes taxes & fees
9.2/10 Wonderful! (781 reviews)
"Bed comfort"

Reviewed on Aug. 9, 2025

La Quinta Inn & Suites by Wyndham 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 $139 per night from Aug 17 to Aug 18
CA $139
CA $165 total
Aug 17 - Aug 18
includes taxes & fees
8.4/10 Very Good! (947 reviews)
"Very convenient. Nice front desk employee but needed to wait a while for multiple people checking in. Loved the lobby/bar but did not have time to take advantage. My only complaint is that the option for breakfast should be described to everyone checking in."

Reviewed on Aug. 9, 2025

Courtyard by Marriott Middletown Goshen
See all 1,418 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
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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 $521 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.