Middleway Trips (flight + hotel)

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    Better together
    Save up to P 3,118 when you book a flight and hotel together*
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    Find the right fit
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    Plan, book, and manage your trip all in one place

Top hotels in Middleway

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 P5,881 per night from Jul 20 to Jul 21
P5,881
P6,398 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (2,068 reviews)
Would stay again!
"Very nice hotel. Super clean and comfortable. Friendly staff. Nice breakfast bar as well."

Reviewed on Jun 23, 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 P3,913 per night from Jul 10 to Jul 11
P3,913
P4,258 total
Jul 10 - Jul 11
includes taxes & fees
8.2/10 Very Good! (1,104 reviews)
"Very clean and eco-friendly…. Loved the waffles for breakfast!!!! Super bonus!!!"

Reviewed on Jun 21, 2025

Travelodge by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHG
3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is P5,274 per night from Jul 6 to Jul 7
P5,274
P5,908 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Our room was comfortable and had many amenities such as a refrigerator and microwave. The staff were welcoming and friendly. Although we were not happy that the restaurant was closed for dinner, the breakfast was wonderful."

Reviewed on Jun 22, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 669 properties in Middleway
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 Middleway vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Middleway costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Middleway?
January, February and November are the best times to look for cheap Middleway vacation packages. Opting to travel in quieter months means you can typically find better prices on hotels and flights.
How many days is enough for Middleway?
The ideal duration of your Middleway vacation depends on what you'd like to see. Generally, a handful of days to a week will give you time to go to all the major attractions and discover some hidden gems along the way.
How to find the best Middleway package deals?
Finding a cheap Middleway package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Middleway package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Middleway vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Middleway vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Middleway?
If you've got your Middleway travel dates confirmed, book as soon as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Middleway?

  1. Pick your travel dates: The things you want to do in Middleway and your preferred season can help you decide when to go.
  2. Set your budget: Factor in costs like flights, meals and transportation when working out how much to set aside for your trip to Middleway. Then, choose a hotel that works with your budget, whether that's an economical option or a high-end getaway.
  3. Decide how many days away: Start by listing all the attractions you'd like to experience in Middleway. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Middleway vacation package that brings all your bookings together.

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