A historic tower with a rounded top and arched windows.

Middletown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • 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

When a city getaway is calling, answer it with a vacation package to Middletown. The neighborhood of Sandy Hook, which is good for nature, history and walking, makes a great base for your adventures. Make your trip to Middletown even more fun by going sightseeing. PNC Bank Art Center, Count Basie Theater and Sandy Hook Gateway National Recreation Area are some of the popular attractions you'll want to explore. A few clicks is all it takes to build your dream Middletown vacation on Expedia.

Top Middletown vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Jan 10 - Jan 13

    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)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $2,352
    CA $1,483
    per traveller
    found 1 day ago
    JW Marriott Essex House New York
  • Jan 15 - Jan 17

    The St. Regis New York + Flight

    Manhattan
    2 nights
    5.0 star property
    9.2/10 - Wonderful (295 reviews)
    "The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"
    Reviewed November 6, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - JFK • Nonstop JFK - YYZ • 1 stop
    CA $2,682
    CA $1,531
    per traveller
    found 1 day ago
    The St. Regis New York
  • Dec 21 - Dec 26

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    5 nights
    4.0 star property
    9.2/10 - Wonderful (4,158 reviews)
    "Everything and everyone was amazing"
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $3,599
    CA $2,080
    per traveller
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square
  • Dec 20 - Dec 24

    Eurostars The Chemists’ Club Hotel + Flight

    Manhattan
    4 nights
    4.0 star property
    9.4/10 - Exceptional (566 reviews)
    "Large room and very clean overall property! Staff was very friendly and was able to accommodate an early check in (without request)."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $3,020
    CA $1,759
    per traveller
    found 1 day ago
    Eurostars The Chemists’ Club Hotel
  • Dec 16 - Dec 20

    1 Hotel Brooklyn Bridge + Flight

    Brooklyn
    4 nights
    5.0 star property
    9.2/10 - Wonderful (1,001 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $4,777
    CA $2,969
    per traveller
    found 1 day ago
    1 Hotel Brooklyn Bridge

Discover the most popular places to visit in Middletown

Middletown Hotel Deals

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.

Frequently Asked Questions

How much does a Middletown vacation package cost?

You'll find cheap prices from CA $1,483 on Expedia for your Middletown getaway. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Middletown costs.

What are the cheapest months to go to Middletown?

If you'd like to snag a cheap Middletown vacation package, consider planning a trip in February, March and November. You'll typically find better prices on accommodations and flights during these months — ideal for a budget-friendly getaway.

How many days is enough for Middletown?

With around 2 days, you'll have enough time to visit popular neighbourhoods such as Port Monmouth and Navesink during your Middletown vacation. Remember to also add Ideal Beach and Mount Mitchell Scenic Overlook to your sightseeing itinerary. In the mood for more adventures? Consider venturing outside of Middletown on day trips and tours.

How to find the best Middletown package deals?

Bagging a cheap Middletown package deal is a breeze with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Middletown package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.

Is it cheaper to book a Middletown vacation as a package?

Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component individually. And you'll still get the freedom to create a personalized Middletown vacation by choosing your favourite accommodation type, airline and car class.

When to book a vacation package to Middletown?

Land incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Middletown adventure.

How to plan a trip to Middletown?

  1. Choose when to go: Check your calendar and get packing. Your preferred time of year and the available activities will also help you decide when to escape to Middletown.
  2. Set your budget: Consider expenses like transportation, flights and meals when working out how much to set aside for your trip to Middletown. Then, pick a hotel that matches your budget, whether that's a low-cost stay or a deluxe getaway.
  3. Set the duration of your trip: Start by listing all the activities and attractions you'd like to experience in Middletown. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Middletown vacation package that brings all your bookings together.

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