A lake surrounded by autumn-colored trees reflecting on the water.

Middletown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.
  • A rooftop terrace with outdoor seating, a city view, and a brick building.
    Jan 14 - Jan 17

    JW Marriott Essex House New York + Flight

    Manhattan
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,000 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $2,033
    CA $1,114
    per traveller
    found 1 day ago
    JW Marriott Essex House New York
  • A hotel room with a desk, chair, and a view of the cityscape through large windows.
    Jan 10 - Jan 15

    Eurostars The Chemists’ Club Hotel + Flight

    Manhattan
    5 nights
    4.0 star property
    9.4/10 - Exceptional (564 reviews)
    Roundtrip • Montreal (YUL) - New York (JFK)
    YUL - LGA • 1 stop LGA - YUL • 1 stop
    CA $2,739
    CA $1,621
    per traveller
    found 1 day ago
    Eurostars The Chemists’ Club Hotel
  • The entrance of Hotel Wall Street with a black facade, large windows, and two potted plants.
    Dec 26 - Dec 31

    Eurostars Wall Street + Flight

    Manhattan
    5 nights
    4.0 star property
    8.0/10 - Very good (1,001 reviews)
    "Cons: Air conditioning never really worked well. Thankfully opening the window helped. It's kind of set up like an apartment so there isn't an ice machine on the floor. The TV was tiny and hard to watch. Breakfast wasn't complimentary ($19 per person). IDK for $2200 I expected a higher caliber of service and amenities. Pros: The staff was always helpful. The location is convenient especially for things downtown close the the financial district."
    Reviewed November 3, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    Save 100% on your flight
    CA $3,573
    CA $2,179
    per traveller
    found 1 day ago
    Eurostars Wall Street
  • A swimming pool with city views, large windows, and potted plants.
    Dec 30 - Jan 2

    Mandarin Oriental, New York + Flight

    Manhattan
    3 nights
    5.0 star property
    9.2/10 - Wonderful (677 reviews)
    "Excellent stay"
    Reviewed October 26, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $5,180
    CA $3,335
    per traveller
    found 1 day ago
    Mandarin Oriental, New York
  • Lobby
    Jan 10 - Jan 15

    Lotte New York Palace + Flight

    Manhattan
    5 nights
    4.5 star property
    9.0/10 - Wonderful (2,359 reviews)
    Roundtrip • Montreal (YUL) - New York (JFK)
    YUL - LGA • 1 stop LGA - YUL • 1 stop
    CA $2,565
    CA $1,701
    per traveller
    found 1 day ago
    Lotte New York Palace

Discover the most popular places to visit in Middletown

A large Ferris wheel against a sunset sky.

Orange County Fairgrounds

8.0/10 (87 reviews)
Enjoy an outing to Orange County Fairgrounds during your stay in Mechanicstown. Discover the area's festivals and churches.
See properties

Middletown Hotel Deals

A breakfast area with a counter displaying hard-boiled eggs, a bowl of green apples, and various pastries.

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
3.5 km from Middletown
8.6 out of 10, Excellent, (1,002 reviews)
The price is CA $123
CA $146 total
includes taxes & fees
Nov 29 - Nov 30
Tru by Hilton 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.
See all properties 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 $1,114 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.