Middletown Vacations

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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.

Discover the most popular places to visit in Middletown

Beautiful drive up to this plantation. You can take a tour of it as well.

Belle Grove Plantation

3.5/5(3 reviews)

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

Cedar Creek and Belle Grove National Historical Park

Explore the great outdoors at Cedar Creek and Belle Grove National Historical Park, a lovely green space in Middletown. Stroll along the riverfront or experience the area's entertainment venues.

Cedar Creek and Belle Grove National Historical Park

Cedar Creek Battlefield Foundation

4.5/5(2 reviews)

You can find out about the history of Middletown with a visit to Cedar Creek Battlefield Foundation. Stroll along the riverfront or experience the entertainment venues in this vibrant area.

Cedar Creek Battlefield Foundation

Middletown Hotel Deals

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $86 total per night from Jan 4 to Jan 5
$86 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (1,405 reviews)
Great price clean and friendly

Reviewed on Dec 28, 2025

Microtel 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
$68 nightly
The price is $74 total per night from Jan 1 to Jan 2
$74 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.4/10 Very Good! (1,084 reviews)
Hotels well Located off 81 for a nice pull Off and overnight stay. Staff is friendly and helpful and rooms comfortable and quiet.

Reviewed on Dec 23, 2025

Travelodge by Wyndham Winchester
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
$99 nightly
The price is $107 total per night from Jan 4 to Jan 5
$107 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,238 reviews)
Staff is very pleasant and personable.

Reviewed on Dec 28, 2025

La Quinta Inn & Suites by Wyndham Winchester
See all 603 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
Population
1,300
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Skyline Caverns, Shenandoah River State Park and Cedar Creek and Belle Grove National Historical Park

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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 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?
If you're looking to snag a cheap Middletown vacation package, consider visiting in January, March and December. You'll usually find lower rates on flights and accommodations during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Middletown?
With a well-organized travel plan, you can easily tick off the top Middletown attractions in a few days. But if you'd like to discover lesser-known spots or go on day tours, consider booking your Middletown vacation for longer.
Is it worth booking a vacation package to Middletown?
Middletown offers everything you need for a wonderful escape. Begin your Middletown vacation on a high note by exploring major attractions like Belle Grove Plantation.
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.
Does Expedia offer Book Now, Pay Later Middletown vacation packages?
If you're anything like us, you love going away but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Middletown trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

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