Stephenson Vacations from $267
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
The Churchill Hotel near Embassy Row
Northwest
$267
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,008 reviews)
Ms. Deborah was very nice and welcoming. It was the day we went to check out was the problem. The young lady who was white treated us like we were the problem because we wanted to check out early. She informed us that she couldn’t check us out until the next day because this was a third party booking. She stated she had to keep our credit card open until our original date to check out.
The bedroom door did not shut close and the air condition continually ran on high, so you froze or shut it off and be hot.
Reviewed on Oct 1, 2026
Stay near popular Stephenson attractions
Frederick County Fairgrounds
Enjoy an outing to Frederick County Fairgrounds during your stay in Stephenson.
Stephenson Hotel Deals
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
$71 nightly
$78 total
Oct 5 - Oct 6
Total with taxes and fees
8.8/10 Excellent! (1,072 reviews)
"Room was clean and efficient. Good for a bed and shower but the breakfast was toast, dry cereal or a waffle. We went to Cracker Barrel."
Reviewed on Oct 2, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
$130 nightly
$148 total
Oct 11 - Oct 12
Total with taxes and fees
Quality Inn Harpers Ferry - Charles Town
25 Union St Harpers Ferry WV
Fully refundable
$89 nightly
$99 total
Oct 26 - Oct 27
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
"Staff were very helpful and the stay very comfortable."
Reviewed on Oct 2, 2026
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
Stephenson Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theater |
More vacations you might like
Frequently asked questions
How much does a Stephenson vacation package cost?
Offering great value package deals from $267 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.
