Middletown Vacation Packages

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Your Middletown Vacation

Let our vacation packages to Middletown inspire your next escape. You'll find a whole lot to like about this vibrant city, starting with the neighborhood of Shawnee Land, which is good for hiking and nature. Any trip to Middletown needs a well-thought-out itinerary. Fill yours with leading attractions like Jacksons Chase Golf Course, Blue Ridge Shadows Golf Club and Belle Grove Plantation. Don't put off exploring this destination any longer. Your ultimate Middletown vacation is a few clicks away with Expedia.

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Middletown Hotel Deals

Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is CA $123 per night from Aug 26 to Aug 27
CA $123
CA $150 total
Aug 26 - Aug 27
includes taxes & fees
9.2/10 Wonderful! (393 reviews)
"Rooms and property were beautiful. Wish they provided garbage cans and ash trays for outdoor seating."

Reviewed on Aug. 21, 2025

Wayside Inn
Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2 out of 5
91 Reliance Road, Middletown, VA
Fully refundableReserve now, pay when you stay
The price is CA $93 per night from Sep 3 to Sep 4
CA $93
CA $103 total
Sep 3 - Sep 4
includes taxes & fees
5.6/10 (286 reviews)
"Great place to sleep and its was very quiet."

Reviewed on Jun. 24, 2025

Econo Lodge Inn & Suites
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Sep 1 to Sep 2
CA $142
CA $154 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (2,130 reviews)
"A"

Reviewed on Aug. 22, 2025

La Quinta Inn & Suites by Wyndham Winchester
See all 606 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
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Frequently asked questions

How much does a Middletown vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Middletown costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Middletown?
If you'd like to score a cheap Middletown vacation package, consider travelling in January, February and June. You'll typically find lower rates on flights and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Middletown?
With a well-planned schedule, you can easily tick off the top Middletown attractions in a handful of days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Middletown vacation for longer.
How to find the best Middletown package deals?
Finding a cheap Middletown package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Middletown package deals. Want a simple trick to score even more 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 cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Middletown vacation by choosing your preferred airline, accommodation type and car class.
How to plan a trip to Middletown?

  1. Choose your travel dates: The things you'd like to do in Middletown and your preferred season can help you decide when to go.
  2. Plan your budget wisely: Besides the price of your stay, you should factor in other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that could arise during your trip to Middletown.
  3. Decide how many days away: Start by listing all the activities and sights you want to experience in Middletown. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Middletown vacation package.

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