Middletown Vacations from $524
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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
- Econo Lodge Inn & Suites Middletown - Winchester South
Dec 10 - Dec 13Econo Lodge Inn & Suites Middletown - Winchester South + Flight
Middletown3 nights2.0 star property5.8/10 - (334 reviews)Roundtrip • Bakersfield (BFL) - Martinsburg (MRB)BFL - IAD • 1 stop IAD - BFL • 1 stop$533$524found 22 hours agoper traveler - Wayside Inn
Dec 10 - Dec 13Wayside Inn + Flight
Middletown3 nights3.5 star property9.2/10 - Wonderful (465 reviews)Roundtrip • Bakersfield (BFL) - Martinsburg (MRB)BFL - IAD • 1 stop IAD - BFL • 1 stop$564$527found 22 hours agoper traveler
Where to stay near Middletown
Winchester
Discover Winchester, a charming destination perfectly suited for adventurous families and culture enthusiasts who will appreciate its rich history and scenic beauty. With attractions like the Shenandoah University, the Museum of the Shenandoah Valley, and the Shenandoah Valley Discovery Museum, there's plenty to explore and enjoy. Located about 14 miles by car from Middletown, Winchester offers easy access to outdoor recreation and cultural experiences, making it a smart choice for your stay.
Front Royal
Experience the charm of Front Royal, an excellent hub for weekend getaway enthusiasts and families who want to immerse themselves in nature and adventure. With attractions like the scenic Shenandoah River, the intriguing Skyline Caverns, and the historic Belle Boyd Cottage, Front Royal offers a blend of outdoor activities and cultural experiences. Located about 9 miles by car from Middletown, this destination makes for a smart choice for travelers seeking a memorable escape.
Strasburg
Make the most of your visit by staying in Strasburg, a haven for history enthusiasts and nature lovers thanks to its rich heritage and stunning scenery. Explore the historic Belle Grove Plantation, wander along the scenic Shenandoah River, and delve into the past at the Strasburg Museum. Located about 5 miles by car from Middletown, Strasburg offers easy access to outdoor adventures and family-friendly activities year-round, making it a smart choice for your vacation stay.
Stephens City
Optimized for families and outdoor enthusiasts, Stephens City stands out as a prime spot for travelers interested in adventure and scenic experiences. With attractions like the historic Shenandoah University, the whimsical Dinosaur Land theme park, and the picturesque Shenandoah River, there's plenty to explore. Located about 5 miles by car from Middletown, this charming city offers easy access to recreational areas and shopping. Booking a stay in Stephens City ensures a delightful base for your Virginia getaway.
Canterburg
Travelers visiting the area often choose Canterburg as their ideal base, especially those with a love for history, family, and nature. This charming village offers easy access to scenic spots like the Shenandoah River, the whimsical Dinosaur Land theme park, and the historic Shenandoah University. With its picturesque marina and lake, Canterburg provides a perfect backdrop for outdoor adventures or a romantic getaway. Located about 10 miles by car from Middletown, it’s a smart choice for a memorable stay.
Discover the most popular places to visit in Middletown
Middletown Hotel Deals
Econo Lodge Inn & Suites Middletown - Winchester South
Econo Lodge Inn & Suites Middletown - Winchester South
Ramada by Wyndham Strasburg/Shenandoah Valley
Ramada by Wyndham Strasburg/Shenandoah Valley"Arrived there and they said they never received my room number requested and on check out they use a kiosk and said I had to contact the 3rd party I booked the hotel through to get a receipt for the stay"
Holiday Inn Express Winchester South-Stephens City by IHG
Holiday Inn Express Winchester South-Stephens City by IHG
Quality Inn Stephens City - Winchester South
Quality Inn Stephens City - Winchester South
Fairfield Inn & Suites Strasburg Shenandoah Valley
Fairfield Inn & Suites Strasburg Shenandoah Valley"You could hear people in the other rooms easily. Fairfield is promoted for having quieter rooms so this was surprising. The breakfast was severely substandard as well. This hotel is also close to a highway but also, apparently locals like to use the Old Valley Pike as their midnight raceway."
"We were very impressed with the breakfast staff. They were amazing. Very friendly , very courteous, and kept the area well cleaned and supplied. What a wonderful way to start the day. Many thanks. Overall, an outstanding place to stay. Will be back again."
Comfort Inn & Suites Winchester
Comfort Inn & Suites Winchester"Propreté. Café pas buvable."
Find out more about Middletown
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.
Frequently Asked Questions
How much does a Middletown vacation package cost?
Offering great value package deals from $524 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.