Middletown Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Samantha Keyes
    deals illustration

    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Middletown Vacation Packages

Middletown Hotel Deals

Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is ₩145,682 per night from Jul 20 to Jul 21
₩145,682
₩174,549 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (391 reviews)
"We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere."

Reviewed on Jul 7, 2025

Wayside Inn
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 ₩160,819 per night from Jul 20 to Jul 21
₩160,819
₩174,970 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (2,083 reviews)
"Always good! On Hotel.com we can read free breakfast every day 6am to 9am. So, on weekend the breakfast begin at 7am. That was too late for us."

Reviewed on Jul 13, 2025

La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is ₩95,734 per night from Jul 20 to Jul 21
₩95,734
₩104,170 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (1,105 reviews)
"The value of this property was great. For the price paid we feel we received a very good room to sleep in for one night on a road trip. Breakfast was better than others in this price range. We drove 1.5 miles to Old Town Winchester for dinner and it was interesting and fun to walk through. The only ..."

Reviewed on Jul 16, 2025

Travelodge by Wyndham Winchester
See all 595 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.

Frequently asked questions

How much does a Middletown vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Middletown costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Middletown?
January, February and June are the best times to search for cheap Middletown vacation packages. Opting to travel in quieter months means you can typically find reduced prices on accommodations and flights.
How many days is enough for Middletown?
With a well-planned schedule, you can easily visit the most popular Middletown attractions in a few days. But if you'd like to explore off the beaten track or go on day trips, think about booking your Middletown vacation for longer.
How to find the best Middletown package deals?
Use Expedia's handy filters to find some of the best Middletown package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Middletown package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Middletown vacation as a package?
You can enjoy significant savings on your next Middletown escape by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Middletown?
Land amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Middletown adventure.
How to plan a trip to Middletown?

  1. Pick the best time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Middletown.
  2. Budget wisely: As well as the cost of your stay, you should consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Middletown.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you'd like to get to in Middletown. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your accommodations and airfare: After you've settled on your travel dates and duration, lock in the perfect 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.