Stephenson Holidays

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    Better together

    Save up to S$134 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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Top hotels in Stephenson

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 1 Sept to 2 Sept
S$145
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,123 reviews)
"One of our fave places to stay when we visit Winchester."

Reviewed on 10 Aug, 2025

La Quinta Inn & Suites 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$128 per night from 31 Aug to 1 Sept
S$128
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"Very nice staff, clean. Restaurant on premises with good bkfst"

Reviewed on 11 Aug, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is S$111 per night from 2 Sept to 3 Sept
S$111
2 Sept - 3 Sept
includes taxes & fees
9/10 Wonderful! (1,324 reviews)
Economical, spotless
"Great price , spotlessly clean. Have stayed here several times for one night, will stay again!"

Reviewed on 10 Aug, 2025

Microtel Inn & Suites by Wyndham Winchester
See all 660 properties in Stephenson
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 Stephenson holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Stephenson costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Stephenson?
January, February and November are great times to look for cheap Stephenson holiday packages. Opting to travel in quieter months means you'll typically find lower prices on hotels and flights.
How many days is enough for Stephenson?
The ideal length for your Stephenson holiday depends on what you'd like to see and do. Usually, a handful of days to a week will give you enough time to visit all the top attractions and explore some hidden spots along the way.
How to find the best Stephenson package deals?
Begin your search for a Stephenson package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Stephenson package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Stephenson adventure off to a flying start.
Is it cheaper to book a Stephenson holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalised Stephenson holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Stephenson?
Score incredible discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Stephenson adventure.
How to plan a trip to Stephenson?

  1. Choose your travel dates: The things you plan to do in Stephenson and your favourite season can help you decide when to get away.
  2. Plan your budget wisely: On top of the price of your hotel, you'll need to factor in other expenses. These include transportation, flights and food. Also, set aside a little extra for unexpected expenses that may arise during your trip to Stephenson.
  3. Decide how long to go away for: Now that you're more familiar with Stephenson, you can figure out the ideal length of your holiday. Put together a rough plan and give yourself enough time for all the things you want to do.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Stephenson 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.