Middletown Vacations

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Find the Best Middletown Vacation Packages

Middletown Hotel Deals

Wayside Inn
Wayside Inn
3.5 out of 5
7783 Main St, Middletown, VA
The price is SAR 362 per night from Apr 26 to Apr 27
SAR 362
SAR 437 total
includes taxes & fees
26 Apr - 27 Apr
9.2/10 Wonderful! (376 reviews)
"Was a very fun atmosphere with and employees and also other guess very nice and friendly and excellent wings"

Reviewed on 2 February 2025

Wayside Inn
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is SAR 351 per night from Apr 27 to Apr 28
SAR 351
SAR 382 total
includes taxes & fees
27 Apr - 28 Apr
9/10 Wonderful! (1,961 reviews)
Great value for money
"New room, a lot of space, clean. Good towers. Perfect. Good breakfast"

Reviewed on 23 April 2025

La Quinta Inn & Suites by Wyndham Winchester
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is SAR 367 per night from May 11 to May 12
SAR 367
SAR 399 total
includes taxes & fees
11 May - 12 May
9.2/10 Wonderful! (1,014 reviews)
"Clean, comfortable room. Relatively quiet"

Reviewed on 23 April 2025

Comfort Inn & Suites
See all 586 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 vacation package cost?
Offering great value package deals 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?
January, February and June are the best times to search for cheap Middletown vacation packages. Opting to travel in quieter months means you can typically find reduced prices on accommodations and flights.
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.
How to plan a trip to Middletown?

  1. Pick the best time to travel: Your schedule, favorite 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 accommodations and airfare: After you’ve settled on your travel dates and duration, lock in the perfect Middletown vacation package for you.

Discover the most popular places to visit in Middletown

Beautiful drive up to this plantation. You can take a tour of it as well.

Belle Grove Plantation

3.5/5(3 reviews)

Learn about the local 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 Battlefield Foundation

4.5/5(2 reviews)

You can find out 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

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