Middleway Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    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 S$145 per night from 6 Jul to 7 Jul
S$145
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (2,045 reviews)
"The staff was very friendly and the room was comfortable and clean."

Reviewed on 8 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 S$96 per night from 2 Jul to 3 Jul
S$96
2 Jul - 3 Jul
includes taxes & fees
8.2/10 Very Good! (1,105 reviews)
"Nice"

Reviewed on 9 Jun, 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 S$134 per night from 15 Jun to 16 Jun
S$134
15 Jun - 16 Jun
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Convenient stop while on a road trip. Hotel was clean, located near many places to eat and shop."

Reviewed on 7 Jun, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 667 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 holiday package cost?
Offering great value package deals on Expedia, you’ll be surprised at how little a holiday to Middleway costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Middleway?
January, February and November are the best times to look for cheap Middleway holiday 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 holiday 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 personalise your search by “Amenities,” “Property type,” “Traveller 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 travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Middleway holiday as a package?
Expedia holiday 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 holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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 holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.