Middletown Trips (flight + hotel)

Photo by Samantha Keyes

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Top hotels in Middletown

Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is P5,363 per night from Aug 19 to Aug 20
P5,363
P6,482 total
Aug 19 - Aug 20
includes taxes & fees
9.2/10 Wonderful! (392 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 P5,822 per night from Sep 1 to Sep 2
P5,822
P6,335 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (2,123 reviews)
"One of our fave places to stay when we visit Winchester."

Reviewed on Aug 10, 2025

La Quinta Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is P4,880 per night from Aug 17 to Aug 18
P4,880
P5,480 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"Very nice staff, clean. Restaurant on premises with good bkfst"

Reviewed on Aug 11, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 610 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.

Popular places to visit

Belle Grove Plantation

Belle Grove Plantation

Learn about the local history of Middletown when you spend time at Belle Grove Plantation. Wander the riverfront or discover the mountain views in this vibrant area.

Belle Grove Plantation

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.