Middletown Vacations from $520

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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.

The Latest Middletown vacation packages

Price found within the past 48 hours. Click for updated prices.
Econo Lodge Inn & Suites
Wayside Inn
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Middletown Hotel Deals

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
$90 nightly
The price is $98 total per night from Feb 10 to Feb 11
$98 total
Feb 10 - Feb 11
Total with taxes and fees
9.2/10 Wonderful! (2,251 reviews)
Very Friendly staff and clean rooms!

Reviewed on Jan 25, 2026

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
$68 nightly
The price is $74 total per night from Feb 10 to Feb 11
$74 total
Feb 10 - Feb 11
Total with taxes and fees
8.4/10 Very Good! (1,071 reviews)
Good value, clean, comfortable bed. Bathroom fan was connected to light so couldnt leave light on in the bathroom as a night light. Fan was loud. All in all..id stay there again when traveling.

Reviewed on Jan 20, 2026

Travelodge by Wyndham Winchester
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
$85 nightly
The price is $92 total per night from Feb 2 to Feb 3
$92 total
Feb 2 - Feb 3
Total with taxes and fees
9/10 Wonderful! (1,441 reviews)
Perfect for a single night, relatively clean, very friendly staff and decent breakfast.

Reviewed on Jan 18, 2026

Microtel Inn & Suites by Wyndham Winchester
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

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.5°F (-0.3°C)Light RainMostly SunnyAverageSlightly Low
February35.1°F (1.7°C)Light RainMostly SunnySlightly LowSlightly Low
March42.6°F (5.9°C)Light RainMostly SunnyAverageAverage
April53.2°F (11.8°C)Light RainMostly SunnyAverageAverage
May62.6°F (17.0°C)Light RainMostly SunnyAverageSlightly High
June70.9°F (21.6°C)Light RainMostly SunnySlightly HighSlightly High
July75.7°F (24.3°C)Light RainMostly SunnySlightly HighAverage
August73.4°F (23.0°C)Light RainMostly SunnyAverageAverage
September66.7°F (19.3°C)Light RainMostly SunnySlightly HighAverage
October55.6°F (13.1°C)Light RainMostly SunnyAverageSlightly High
November43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage
December36.7°F (2.6°C)Light RainMostly SunnySlightly LowSlightly Low

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.

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 from $520 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.