Middleway Vacations

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Find the Best Middleway Vacation Packages

Middleway Hotel Deals

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 ₩142,990 per night from Sep 1 to Sep 2
₩142,990
₩155,572 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (2,136 reviews)
"The bedroom was clean. Some area a bit older looking but good. Hall ways a little smelly like needs carpets refreshed. But not all that bad.."

Reviewed on Aug 25, 2025

La Quinta Inn & Suites by Wyndham Winchester
Quality Inn

Quality Inn

2.5 out of 5
25 Union St, Harpers Ferry, WV
Fully refundableReserve now, pay when you stay
The price is ₩113,723 per night from Sep 7 to Sep 8
₩113,723
₩127,370 total
Sep 7 - Sep 8
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"Great location for stay near park. Excellent value. Friendly staff."

Reviewed on Aug 26, 2025

Quality Inn
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 ₩114,281 per night from Sep 1 to Sep 2
₩114,281
₩128,520 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
"Clean and staff was great."

Reviewed on Aug 23, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 668 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.