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.
Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Jun. 25 - Jun. 28
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Newburgh (SWF)
6/10 (1,003 reviews)
Pros: location, staff was very friendly and helpful, room was clean and they had updated decor in room. Cons: not a welcoming approach as lobby entrance is in weird location, NOTE THERE IS NO ELEVATOR(but front desk asked if I’d prefer 1st or 2nd floor room), right next to highway so loud and the patio light is on all night with a curtain that didn’t completely block it. All in all, worth the convenience.

Reviewed on May 24, 2024

Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
Save 100% on your flight
per person
Aug. 9 - Aug. 11
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
9.6/10 Exceptional! (18 reviews)
Good environment view, but the room is just okay in consideration of the price.

Reviewed on Feb. 25, 2024

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
per person
Jul. 19 - Jul. 23
found 2 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
5.2/10 (1,000 reviews)
Smooth, efficient, comfortable, quiet.

Reviewed on Apr. 13, 2024

Newburgh Inn

Newburgh Inn

2 out of 5
per person
Jun. 25 - Jun. 28
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Newburgh (SWF)
3.8/10 (32 reviews)
New owners bought it last year and are remodeling it. Doing a great job. New rooms are really nice.

Reviewed on May 21, 2024

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2.5 out of 5
per person
Jun. 25 - Jun. 28
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Newburgh (SWF)
5.6/10 (1,002 reviews)
Clean and nice always

Reviewed on Apr. 29, 2024

Middletown Hotel Deals

La Quinta Inn & Suites by Wyndham Middletown
La Quinta Inn & Suites by Wyndham Middletown
2.5 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Jun. 4 to Jun. 5
CA $173
CA $205 total
includes taxes & fees
Jun 4 - Jun 5
9.2/10 Wonderful! (387 reviews)
"The staff was nice. Checking in was very quick and the place is clean."

Reviewed on May 22, 2024

La Quinta Inn & Suites by Wyndham Middletown
Tru by Hilton Middletown
Tru by Hilton Middletown
2.5 out of 5
41 Dunning Road, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from May 27 to May 28
CA $169
CA $200 total
includes taxes & fees
May 27 - May 28
8.2/10 Very Good! (687 reviews)
"💪"

Reviewed on May 20, 2024

Tru by Hilton 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 CA $183 per night from Jun. 10 to Jun. 11
CA $183
CA $207 total
includes taxes & fees
Jun 10 - Jun 11
8.6/10 Excellent! (849 reviews)
"Staff very friendly and room spacious and very clean!"

Reviewed on May 19, 2024

Sleep Inn & Suites 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

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Middletown vacation package cost?
From as low as CA $567, you can tailor make your Middletown package. Simply combine hotels, flights and car rentals and we’ll reward you with discounts.
How do I get a cheap travel package to Middletown?
Combine your bookings with Expedia to save on your next big adventure. With more than 550 partner airlines and 1,000,000 hotels throughout the world, your Middletown vacation package can be tailored exactly to suit your travel style. With all that extra money, why not add a few fun tours and experiences? It’s an easy way to unlock even more savings. Your dream vacation in Middletown is closer than you thought!
Where should I stay in Middletown?
With so much to explore in Middletown, we suggest you stay close to its attractions. Orange County Fair Speedway, Orange County Fairgrounds and Galleria at Crystal Run are some interesting ones to add to your must-see list.
What are the top hotels in Middletown?
If you’re planning to stay in the Mechanicstown neighborhood, some excellent options are Holiday Inn Express & Suites Middletown - Goshen, an IHG Hotel and Microtel Inn & Suites by Wyndham Middletown. Scotchtown is another favorite Middletown area. We recommend Courtyard by Marriott Middletown Goshen or Tru by Hilton Middletown if you prefer this end of town.
How far in advance should I book my Middletown vacation?
It depends on the air carrier, but you can usually browse through international fares on Expedia up to 12 months in advance. While it’s a good idea to book ahead of time, lucky travelers will sometimes find a cheaper seat just weeks prior to departure dates.
What does an Expedia Middletown travel package include?
That depends on you. You can pick from a variety of Middletown bundles, such as a hotel, rental car and flight. You can also book a flight and a hotel, or a rental car with a flight. Once you’ve made your booking, you can add on the fun stuff like activities and tours. Whatever your perfect Middletown break looks like, get set to save!
What should I know before booking a Middletown travel package?
Tailor deals that match your budget with an Expedia package. Hotels, flights, rental cars — we’ve got all of them. You’ll save a packet just by combining your bookings. Whether you’re heading away on an adventure in the snow or venturing someplace warm, your ideal getaway is just clicks away.
Can I choose my airline with a Middletown Expedia vacation package?
With a vacation package, you’re in control. Whether you’re eager to fly to Middletown in economy or first class, simply choose from the available airline options. Expedia has access to over 550 partner airlines across the world.
If I'm not able to travel, can I cancel my Middletown vacation package?
It’s hard to predict what tomorrow might bring, so it’s good to know that you can change or cancel your Middletown vacation package. If you made your booking in the last 24 hours, you may be eligible for a refund. If it’s an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Middletown

Image for Orange County Fair Speedway

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
Image for Orange County Fairgrounds

Orange County Fairgrounds

Enjoy an outing to Orange County Fairgrounds during your stay in Mechanicstown. Discover the area's festivals and churches.

Orange County Fairgrounds
Image for Galleria at Crystal Run

Galleria at Crystal Run

During your visit to Middletown, you can search for that perfect souvenir at Galleria at Crystal Run. While in this family-friendly area, you can savor the top-notch restaurants.

Galleria at Crystal Run

What to do in Middletown

Image for LEGOLAND New York Resort Admission Ticket

LEGOLAND New York Resort Admission Ticket

CA $77
Per adult
80% of travellers recommend
LEGOLAND New York Resort Admission Ticket
See all activities in Middletown

Other vacations you might like

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