Stephenson Vacations from $400

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Your Stephenson Vacation

Let our vacation packages to Stephenson inspire your next adventure. You'll find loads to like about this captivating city, starting with the neighborhood of Old Town Winchester, which is good for cafes and history. If your trip to Stephenson includes some sightseeing, take in famous attractions like Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Expedia will help you escape your routine. Tailor your vacation to Stephenson to suit your travel style, whatever that may be.

The Latest Stephenson vacation packages

Price found within the past 48 hours. Click for updated prices.
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Stephenson Hotel Deals

Hampton Inn Martinsburg

Hampton Inn Martinsburg

2.5 out of 5
975 Foxcroft Ave Martinsburg WV
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $106 total per night from Apr 9 to Apr 10
$106 total
Apr 9 - Apr 10
Total with taxes and fees
8.8/10 Excellent! (1,010 reviews)
Staff was extremely friendly and helpful! Loved the welcoming message from the front desk. Would definitely stay again!

Reviewed on Mar 15, 2026

Hampton Inn Martinsburg
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
$91 nightly
The price is $99 total per night from Mar 22 to Mar 23
$99 total
Mar 22 - Mar 23
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
Very clean, nice bar/restaurant, convenient location. Excellent breakfast! Will definitely stay again when traveling 😄

Reviewed on Mar 14, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $138 total per night from Mar 23 to Mar 24
$138 total
Mar 23 - Mar 24
Total with taxes and fees
9.4/10 Exceptional! (1,007 reviews)
Great stay!

Reviewed on Mar 15, 2026

The George Washington Hotel, A Wyndham Grand Hotel
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.

Find the Best Stephenson Vacation Packages

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Frequently asked questions

How much does a Stephenson vacation package cost?
Offering great value package deals from $400 on Expedia, you'll be thrilled with how little a vacation to Stephenson costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Stephenson?
December, January and February are great times to search for cheap Stephenson vacation packages. Choosing to travel in less busy periods means you can generally find reduced prices on accommodations and flights.
How many days is enough for Stephenson?
Usually, a handful of days is enough to explore the major sights during your Stephenson vacation. But if you want to have more time to unwind or take day trips, think about extending your trip.
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 vacation as a package?
Expedia vacation 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 personalized Stephenson vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Stephenson vacation packages?
Set off on your perfect escape to Stephenson with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait for your next paycheck — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily stay on budget and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.