Middletown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Stephanie Sutton
    deals illustration

    Better together

    Save up to £335 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

Your Middletown Holiday

Let our holiday packages to Middletown inspire your next escape. You'll find a whole lot to like about this vibrant city, starting with the neighbourhood 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 holiday is a few clicks away with Expedia.

Middletown Essential Information

Language
English
Currency
U.S dollars
Population
1,300
Max Temp Winter
4ºC
Max Temp Summer
29ºC
Top Sights
Skyline Caverns, Shenandoah River State Park and Cedar Creek and Belle Grove National Historical Park

Top hotels in Middletown

Wayside Inn
Wayside Inn
3.5 out of 5
7783 Main St, Middletown, VA
The price is £78 per night from 27 Jul to 28 Jul
£78
27 Jul - 28 Jul
includes taxes & fees
9.2/10 Wonderful! (391 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 7 Jul 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 £93 per night from 20 Jul to 21 Jul
£93
20 Jul - 21 Jul
includes taxes & fees
9/10 Wonderful! (2,078 reviews)
"Walk in shower convenient. The pillows are uncomfortable, lumpy."

Reviewed on 10 Jul 2025

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
The price is £56 per night from 16 Jul to 17 Jul
£56
16 Jul - 17 Jul
includes taxes & fees
8.4/10 Very Good! (1,100 reviews)
"Staff friendly and helpful.. room was clean and bed very comfortable."

Reviewed on 9 Jul 2025

Travelodge by Wyndham Winchester
See all 595 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Middletown travel package cost?
The most affordable Middletown travel package is , so your dream getaway can become a reality --- without it costing a fortune. Combine flights, hotels and car rentals to customize a package suited to your travelling style.
If I'm not able to travel, can I cancel my Middletown travel package?
If your travel plans in Middletown have been upended, it's a relief to know that it's possible to amend or cancel your booking. If your booking was made within the last 24 hours, you may be able to get a refund. If your booking is older than that, your hotel, airline or car rental company may impose fees. To find out more, visit our Customer Service Portal.
How do I get a cheap travel package to Middletown?
Booking a flight and hotel together with Expedia won't just save you time --- it'll save you money too. A Middletown travel package makes it a cinch to organise the ideal trip. With more than 550 airlines throughout the world to pick from, finding convenient flights that suit your schedule won't be hard. Not only that, we've got over 1,000,000 properties globally to take your pick of. Talk about choice! Whatever your budget, Expedia will help show you the world.
Does Expedia offer Book Now, Pay Later Middletown holidays?
Expedia has teamed up with online lender Klarna to make your next getaway easier on your hip pocket. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more money to spend while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that fits into your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that fit all budgets, so you can book that well-deserved holiday now.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then select this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan with Klarna.

Where should I stay in Middletown?
You'll want to stay where the action is. Many visitors like to book hotels in the vicinity of top attractions, such as Jacksons Chase Golf Course, Belle Grove Plantation and Cedar Creek and Belle Grove National Historical Park.
What are the top hotels in Middletown?
If it's your first visit to Middletown, reserve a room at DoubleTree by Hilton Front Royal Blue Ridge Shadows or TownePlace Suites by Marriott Front Royal. Both offer friendly service and are top options with many travellers.
How far in advance should I book my Middletown holiday?
Reserving your seat early with Expedia means one less thing to have to worry about. A number of air carriers advertise tickets up to 12 months prior to take off. Typically, this is the cheapest time to book. If circumstances have left you booking late, discount prices to Middletown sometimes emerge just a few weeks before departure.
What does an Expedia Middletown travel package include?
With Expedia, you can choose any combination of car rentals, hotels and flights to build your ideal Middletown travel package. Once you've made your booking, you can add on the fun stuff like sightseeing tours and activities. Remember, the more you bundle, the more dollars you'll save!
What should I know before booking a Middletown travel package?
Whether it's relaxation or adventure you're craving, a Middletown travel package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your accommodation with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Middletown Expedia travel package?
Yes, and with over 550 airlines to pick from worldwide, you have loads of choice. Have a look through the available options and find out which airline best suits your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.