Stephens City Vacations from $281
Book a Hotel + Flight or Car together to unlock savings
Your Stephens City Vacation
Let our vacation packages to Stephens City inspire your next great escape. There's lots to love about this vibrant city, starting with the neighborhood of Old Town Winchester, which is great for cafes and history. Apple Blossom Mall, Dinosaur Land and The Kernstown Battlefield are just some of the many sights worth exploring during your trip to Stephens City. Expedia has what you need to escape the everyday. Tailor your vacation to Stephens City to suit your style of travel, whatever that may be.
The Latest Stephens City vacation packages
Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Baltimore Inner Harbor
Downtown Baltimore
$361
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
5.2/10 (1,000 reviews)
The room was nice and clean, very comfortable and meet our expectations. Evening staff not so friendly but the morning staff was really nice and welcoming. The only thing I didn’t like was swapping out the towels. You have to bring your dirty towels down and swap for clean towels. I feel like housekeeping should bring these to you upon request
Reviewed on Sep 21, 2026
Riggs Washington DC
Downtown Washington D.C.
$566
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,430 reviews)
Staff were amazing, location of property is perfect. Room was functional but would prefer a proper chair or desk chair for seating instead of upholstered ottomans.
Reviewed on Sep 21, 2026
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View all tripsStay near popular Stephens City attractions
Valerie Hill Winery
9.6/10 (5 reviews)
This 1807 Federal-style manor house winery blends Virginia's winemaking with historical elegance. Savor award-winning wines in rooms featuring original heart pine floors while overlooking the scenic Shenandoah Valley.
Appleland Sports Center
9.0/10 (4 reviews)
This family-friendly sports center offers a 12-hole executive golf course and mini-golf in a relaxed setting. Practice your swing at the driving range while enjoying Virginia's countryside.
Stephens City Hotel Deals
Holiday Inn Express Winchester South-Stephens City by IHG
165 Town Run Ln Stephens City VA
Fully refundable
$88 nightly
$98 total
Sep 27 - Sep 28
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
$130 nightly
$148 total
Oct 1 - Oct 2
Total with taxes and fees
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
$69 nightly
$76 total
Sep 23 - Sep 24
Total with taxes and fees
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 Stephens City Vacation Packages
Stephens City Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,950 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
Top Sights | Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theater |
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Frequently asked questions
How much does a Stephens City vacation package cost?
Offering excellent value package deals from $281 on Expedia, you'll be surprised at how little a vacation to Stephens City costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Stephens City?
If you're looking to book a cheap Stephens City vacation package, consider planning a trip in February, September and December. You'll generally find better rates on accommodations and flights during these months — perfect for budget-conscious travelers.
How many days is enough for Stephens City?
Usually, a handful of days is enough to check out the top attractions during your Stephens City vacation. However, if you prefer to have some time to chill out or take day tours, think about extending your trip.
How to find the best Stephens City package deals?
Bagging a cheap Stephens City package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Stephens City package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Stephens City vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still get the freedom to create a customized Stephens City vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Stephens City?
If you have your Stephens City vacation dates confirmed, book early to grab some incredible deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
Does Expedia offer Book Now, Pay Later Stephens City vacation packages?
Your Stephens City break is meant to be an escape from your daily routine, not a reason for money worries. So to allow you extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.