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 Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
Price was CA $649, price is now CA $587 per person
CA $587
per person
Oct 7 - Oct 11
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
6.2/10 (1,005 reviews)
I was very content. Clean room staff was amazing and very clean

Reviewed on Aug. 11, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Price was CA $801, price is now CA $709 per person
CA $709
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
9.2/10 Wonderful! (775 reviews)
We were stranded in Middletown, NY for 3 days due to a tire issue (waiting on special order tire from Sams Club) and it couldn't have been at a better hotel. Was a very pleasant stay.

Reviewed on Aug. 20, 2025

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
Price was CA $721, price is now CA $647 per person
CA $647
per person
Oct 7 - Oct 11
found 1 hour ago
Roundtrip 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

Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
Price was CA $673, price is now CA $607 per person
CA $607
per person
Oct 7 - Oct 11
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
6.4/10 (1,002 reviews)
Well done all around. Good value

Reviewed on Aug. 8, 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
Price was CA $1,463, price is now CA $1,370 per person
CA $1,370
per person
Oct 2 - Oct 7
found 4 hours ago
Roundtrip flight included
Calgary (YYC) to Newburgh (SWF)
8.4/10 Very Good! (1,006 reviews)
This is the second time we have stayed here. The facilities are clean, the room was clean, and the staff was great. Definitely a great place to stay. So you next time!

Reviewed on Aug. 19, 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
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Aug 25 to Aug 26
CA $164
CA $193 total
Aug 25 - Aug 26
includes taxes & fees
9.2/10 Wonderful! (789 reviews)
"Our room...and all areas of the Hotel were very clean and well maintained. Staff was very helpful..and friendly!"

Reviewed on Aug. 17, 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 $142 per night from Sep 3 to Sep 4
CA $142
CA $168 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"Service/staff was nice. Hotel room was clean and adequate."

Reviewed on Aug. 18, 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 CA $152 per night from Aug 25 to Aug 26
CA $152
CA $180 total
Aug 25 - Aug 26
includes taxes & fees
8.4/10 Very Good! (959 reviews)
Marriott upstate NY
"Great place. I would say a 9.5 out of 10. Breakfast was great, just a really long wait. Lots of guests…weddings. Comfortable, safe, clean, priced competitively"

Reviewed on Aug. 17, 2025

Courtyard by Marriott Middletown Goshen
See all 1,426 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

What to do in Middletown

BEST LEGOLAND New York 1-Day Tour from New York

BEST LEGOLAND New York 1-Day Tour from New York

CA $251
per adult
BEST LEGOLAND New York 1-Day Tour from New York
See all activities in Middletown

Frequently asked questions

How much does a Middletown vacation package cost?
You can snap up a vacation package to this top destination from CA $587 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.