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Middletown Vacations from $1,124

Book a Hotel + Flight or Car together to unlock savings

The Latest Middletown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Breakfast area
    Oct 16 - Oct 19

    Econo Lodge Inn & Suites Middletown - Winchester South + Flight

    Middletown
    3 nights
    2.0 star property
    5.8/10 - (326 reviews)
    "Carolyn at the front desk was great and was very helpful. There was no phone in the room for one reason and no cloak radio. Now maybe the radios get stolen but sure. My room was clean and I felt safe and comfortable."
    Reviewed July 28, 2026
    Roundtrip • Southampton (SOU) - Winchester (WGO)
    SOU - IAD • 1 stop IAD - SOU • 1 stop
    $1,159
    $1,124
    per traveler
    found 1 day ago
    Econo Lodge Inn & Suites Middletown - Winchester South
  • Breakfast, lunch, dinner and brunch served
    Oct 16 - Oct 19

    Wayside Inn + Flight

    Middletown
    3 nights
    3.5 star property
    9.2/10 - Wonderful (443 reviews)
    "Full of character"
    Reviewed July 27, 2026
    Roundtrip • Southampton (SOU) - Winchester (WGO)
    SOU - IAD • 1 stop IAD - SOU • 1 stop
    $1,323
    $1,219
    per traveler
    found 1 day ago
    Wayside Inn

Discover the most popular places to visit in Middletown

Belle Grove Plantation

8.4/10 (8 reviews)
This Jeffersonian-inspired Manor House showcases antebellum plantation life and Civil War history. Explore the heritage apple orchard and original outbuildings while enjoying panoramic mountain views.

Middletown Hotel Deals

Breakfast, lunch, dinner and brunch served

Wayside Inn

Wayside Inn
3.5 star property
0.2 mi from Middletown
9.2 out of 10, Wonderful, (443 reviews)
"Full of character"
$144 nightly
The price is $159
Aug 2 - Aug 3
Total with taxes and fees
Wayside Inn
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.
See all properties in Middletown

Frequently Asked Questions

How much does a Middletown vacation package cost?

Offering great value package deals from $1,124 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.

Book with confidence

Things to do in and around Middletown

Middletown, Virginia, is an ideal destination for outdoor enthusiasts and those seeking adventure amidst beautiful scenery. Visitors can enjoy a variety of activities, including exploring recreational areas and hitting the links at local golf courses. Whether you're looking for day tours, romantic getaways, or golf getaways, Middletown offers great vacation options for everyone. Plan your perfect escape and experience the charm and beauty of this quaint town.

Shopping

For a great shopping experience in Middletown, visit Shen-Val Farm Market for local goods, or check out Natural Art Garden Center for unique plants. If you're up for a drive, Apple Blossom Mall offers a variety of shops and entertainment just 11 miles away.

Recreation

Experience the serene landscapes at Jackson's Chase Golf Course, where you can enjoy a round of golf amidst beautiful outdoor vibes. For a cultural escape, visit Wayside Theater for captivating performances. Relax at Appleland Sports Center, a short drive away, offering wellness and rejuvenation activities to unwind.

Adventure

Summit Point Motorsports Park, located 22 miles from Middletown, offers thrilling motor racing experiences for adrenaline junkies. For a family-friendly adventure, visit Watermelon Park Campground, 19 miles away, where outdoor fun awaits. Don't miss the scenic Massanutten Storybook Trail, 25 miles from Middletown, perfect for adventurous hikers.

Nightlife

Middletown's nightlife offers a cozy atmosphere with local bars and eateries. Check out The Main Street Grill for great food and drinks. For live music, visit The Red Fox Inn, where you can enjoy performances while sipping on craft cocktails and mingling with friendly locals.

Find the best attractions in and around Middletown

Middletown, Virginia, is a charming destination for outdoor enthusiasts and families alike, offering scenic views and adventure opportunities. Visitors can explore local attractions such as the visitor center and picturesque rivers, perfect for cultural experiences. While the town is known for its natural beauty, travelers may also want to seek out nearby beaches for relaxation and fun. Whether you’re seeking adventure or family-friendly activities, Middletown has something for everyone.

  • Shenandoah River: Experience the natural beauty of the Shenandoah River, located 8 miles from Middletown. Enjoy scenic views, perfect for fishing, kayaking, or simply relaxing by the water's edge, immersing yourself in the peaceful outdoor vibes.
  • Front Royal Entrance Shenandoah National Park: Just 10 miles away, this visitor center serves as the gateway to adventure. Explore trails and enjoy family-friendly activities amidst stunning landscapes, making it an ideal spot for outdoor enthusiasts.
  • Cedar Creek Battlefield Foundation: Situated within Middletown, this historic site offers a glimpse into the past, rich in culture and history. Learn about the Civil War battles that took place here and engage with interactive exhibits.

Best time to go to Middletown

The best time to visit Middletown is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Tips to save on your trip to Middletown

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Middletown.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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