Middletown Holidays

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Your Middletown Holiday

Come and experience this interesting city for yourself with a Middletown holiday package. Consider spending a few days in the neighbourhood of Shawnee Land, which is good for hiking and nature, and your time here will be nothing short of unforgettable. Fill your spare time with tours of Cedar Creek and Belle Grove National Historical Park, Blue Ridge Shadows Golf Club and Belle Grove Plantation, some of the things you shouldn't miss during your trip to Middletown. Stop daydreaming and start adventuring. Browse the multitude of options on Expedia today and put your Middletown holiday plans into gear!

Middletown Holiday

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

Our pick of the best Middletown Hotel Deals

Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is AU$166 per night from 5 Aug to 6 Aug
AU$166
5 Aug - 6 Aug
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 AU$172 per night from 29 July to 30 July
AU$172
29 July - 30 July
includes taxes & fees
9/10 Wonderful! (2,082 reviews)
Highly recommend
"Hotel was very clean and comfortable. Staff were friendly and helpful. It was very quiet, we didn’t heard anyone. Will definitely stay again if in the area!"

Reviewed on 20 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 AU$115 per night from 27 July to 28 July
AU$115
27 July - 28 July
includes taxes & fees
8.4/10 Very Good! (1,089 reviews)
"Close to Sportsman 's Warehouse. Short drive to Chick-fil-A. Breakfast was good, as we like a light meal. Room was quiet, slept well on comfy bed."

Reviewed on 17 Jul. 2025

Travelodge 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Discover the most popular places to visit in Middletown

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

Frequently asked questions

How much does a Middletown holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Middletown costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Middletown?
January, February and June are the best times to search for cheap Middletown holiday packages. Opting to travel in quieter months means you can typically find reduced prices on accommodation and flights.
How many days is enough for Middletown?
With a well-planned schedule, you can easily visit the most popular Middletown attractions in a few days. But if you'd like to explore off the beaten track or go on day trips, think about booking your Middletown holiday for longer.
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 holiday package well in advance.
Is it cheaper to book a Middletown holiday as a package?
You can enjoy significant savings on your next Middletown escape by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to see some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday 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.
How to plan a trip to Middletown?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Middletown.
  2. Budget wisely: As well as the cost of your stay, you should consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Middletown.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you'd like to get to in Middletown. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your accommodation and airfare: After you've settled on your travel dates and duration, lock in the perfect Middletown holiday package for you.

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