Middletown Vacations from $303

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The Latest Middletown vacation packages

Price found within the past 48 hours. Click for updated prices.
Pony Island Inn

Pony Island Inn

2.5 out of 5
Price was $352, price is now $303 per person
$303
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Manteo (MEO)
9.4/10 Exceptional! (454 reviews)
Great place and affordable! Easy access to everything!

Reviewed on Oct 6, 2025

Blackbeard's Lodge

Blackbeard's Lodge

3.5 out of 5
Price was $458, price is now $376 per person
$376
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Manteo (MEO)
8.4/10 Very Good! (313 reviews)
We had a great stay at this hotel everyone was very n8ce and accommodating

Reviewed on Nov 2, 2025

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Middletown Hotel Deals

Quaint 3BR Newly Renovated Pet-Friendly Private Home on 3 Acres 1hr to OBX

Quaint 3BR Newly Renovated Pet-Friendly Private Home on 3 Acres 1hr to OBX

Fairfield NC
$431 nightly
The price is $486 total per night from Dec 21 to Dec 22
$486 total
Dec 21 - Dec 22
Total with taxes and fees
9.6/10 Exceptional! (12 reviews)
It was great to return to the Fairfield area. This house is in an excellent location, close to the lakes & preserves. The address now brings you directly to the driveway via gps. A few years ago that wasn’t the case. The only critters I saw in the house weren’t cringeworthy at all, a cricket & a ...

Reviewed on Dec 9, 2025

Quaint 3BR Newly Renovated Pet-Friendly Private Home on 3 Acres 1hr to OBX
Beautiful pet friendly lodge in a quaint fishing village and sleeps 16

Beautiful pet friendly lodge in a quaint fishing village and sleeps 16

Engelhard NC
9.8/10 Exceptional! (65 reviews)
Nice for a large group, We had plenty of room for our family of 7. The house was clean and comfy. Roanoke island/Nags Head is about an hour away. The plus side to that is that it’s very quiet with no traffic congestion. The negative is that larger grocery stores are a bit of a drive.

Reviewed on Aug 8, 2025

Get rates
Beautiful pet friendly lodge in a quaint fishing village and sleeps 16
Quaint 3bedroom house in Swan Quarter with WiFi & AC. Close to public boat ramp.

Quaint 3bedroom house in Swan Quarter with WiFi & AC. Close to public boat ramp.

Swan Quarter NC
$206 nightly
The price is $226 total per night from Dec 21 to Dec 22
$226 total
Dec 21 - Dec 22
Total with taxes and fees
10/10 Exceptional! (13 reviews)
We had a good experience at the Swanquarter home. Our communication with Vanessa was friendly and responses were very prompt with information requested.

Reviewed on Dec 7, 2025

Quaint 3bedroom house in Swan Quarter with WiFi & AC. Close to public boat ramp.
See all 10 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.

Find the Best Middletown Vacation Packages

Middletown Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Middletown vacation package cost?
You'll find cheap prices from $303 on Expedia for your Middletown break. However, a range of factors like the hotel choice, length of stay and season will determine 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 traveling in November, December and January. You'll typically find better rates on airfares and hotels during these months — ideal for budget-conscious travelers.
How many days is enough for Middletown?
The ideal length of your Middletown vacation depends on what you'd like to do and see. Usually, a few days to a week will give you plenty of time to visit all the main attractions and discover some hidden gems along the way.
How to find the best Middletown package deals?
Use Expedia's handy filters to find some unbeatable Middletown package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Middletown package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Middletown vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalized Middletown vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Middletown?
Land incredible bargains by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Middletown break.
How to plan a trip to Middletown?

  1. Choose your travel dates: The things you want to do in Middletown and your preferred season will help you decide when to get away.
  2. Set a budget: Consider expenses like flights, food and transportation when calculating how much to save for your trip to Middletown. Then, select a hotel that fits your budget, whether that's an economical stay or a more luxurious getaway.
  3. Organize your Middletown escape with our trip planning tool: Look for and book accommodations and activities all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Middletown together.
  4. Decide how long to go for: Now that you're up to speed on Middletown, you can figure out the perfect length of your break. Pull together a draft plan and give yourself enough time to get through everything on your must-do list.
  5. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Middletown vacation package.
  6. Add on excursions and experiences: Have a look at our travel guide to find some exciting things to do in Middletown. Book tickets or make reservations in advance to save time and skip the hassle of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Middletown vacation packages?
If you're like us, you love jet-setting around the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Middletown break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.