Middletown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Samantha Keyes

Top hotels in Middletown

Wayside Inn
Wayside Inn
3.5 out of 5
7783 Main St, Middletown, VA
The price is 2.742.600 ₫ per night from 28 Jun to 29 Jun
2.742.600 ₫
3.286.027 ₫ total
28 Jun - 29 Jun
includes taxes & fees
9.2/10 Wonderful! (387 reviews)
"If your history buff exploring the area this is your ideal base of operations. Close to many local historical sites and the place itself is a piece of Americana. If the walls could talk in this place who knows what it would tell us about the past. The place is remarkably well kept given its age and ..."

Reviewed on 17 Jun 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 2.708.644 ₫ per night from 1 Jul to 2 Jul
2.708.644 ₫
2.947.120 ₫ total
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (2,067 reviews)
"Easy to get to, quiet, kind staff, clean rooms, great for a quick stop."

Reviewed on 25 Jun 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 1.802.280 ₫ per night from 2 Jul to 3 Jul
1.802.280 ₫
1.961.090 ₫ total
2 Jul - 3 Jul
includes taxes & fees
8.2/10 Very Good! (1,106 reviews)
"Very friendly, professional and knowledgeable clerk. Seemless check in. Clean spacious room."

Reviewed on 25 Jun 2025

Travelodge by Wyndham Winchester
See all 593 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.

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.

Popular places to visit

Belle Grove Plantation

Belle Grove Plantation

Find out about the history of Middletown when you spend time at Belle Grove Plantation. Wander the riverfront or discover the mountain views in this vibrant area.

Belle Grove Plantation

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

Cedar Creek Battlefield Foundation

You can learn about the history of Middletown with a visit to Cedar Creek Battlefield Foundation. Stroll along the riverfront or experience the entertainment venues in this vibrant area.

Cedar Creek Battlefield Foundation