Middletown Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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

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Find the Best Middletown Vacation Packages

Middletown Hotel Deals

Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

2 out of 5
91 Reliance Road Middletown VA
Fully refundable
The price is SARĀ 243 per night from Aug 16 to Aug 17
SARĀ 243
SARĀ 268 total
16 Aug - 17 Aug
includes taxes & fees
5.8/10 (325 reviews)
"Believe the reviews. When we arrived, there was a crack-head in front of us with no money trying to negotiate for a room. The check-in person seemed high and didn't bother to stop vaping as she took my ID and checked us in. When I turned on the A/C in the room, a waft of mildew aroma moved across ..."

Reviewed on 9 July 2026

Econo Lodge Inn & Suites Middletown - Winchester South
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St Middletown VA
The price is SARĀ 456 per night from Jul 20 to Jul 21
SARĀ 456
SARĀ 541 total
20 Jul - 21 Jul
includes taxes & fees
9.2/10 Wonderful! (442 reviews)
"Historic, charming, relaxing."

Reviewed on 14 July 2026

Wayside Inn
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is SARĀ 342 per night from Jul 26 to Jul 27
SARĀ 342
SARĀ 381 total
26 Jul - 27 Jul
includes taxes & fees
TRU By Hilton Winchester
See all 631 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.

Stay near popular Middletown attractions

Belle Grove Plantation

8.4/10 (8 reviews)
This Jeffersonian-inspired Manor House showcases antebellum plantation life and Civil War history. Explore the heritage apple orchard and original outbuildings while enjoying panoramic mountain views.
See properties

Frequently asked questions

How much does a Middletown vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Middletown costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Middletown?
If you'd like to score a cheap Middletown vacation package, consider traveling in January, February and June. You'll typically find lower rates on flights and hotels during these months ā€” perfect for a budget-friendly break.
How to find the best Middletown package deals?
Finding a cheap Middletown package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Middletown package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Middletown vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Middletown vacation by choosing your preferred airline, accommodation type and car class.
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. Choose your travel dates: The things you'd like to do in Middletown and your preferred season can help you decide when to go.
  2. Plan your budget wisely: Besides the price of your stay, you should factor in other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that could arise during your trip to Middletown.
  3. Decide how many days away: Start by listing all the activities and sights you want to experience in Middletown. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Middletown vacation package.