Stephens City Vacations from $450
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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.
Lord Baltimore Hotel
Downtown Baltimore
$450
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (3,160 reviews)
Very interesting had a lot of fun learning about the hotel.Itself, architecture is just beautiful, still, there are some things that could be updated a little.But overall, it was a great stay.
Reviewed on Aug 12, 2026
Lyle Washington D.C.
Northwest
$656
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,663 reviews)
Loved the beautiful neighborhood the hotel is situated in. The valet parking gentlemen were extremely nice and helpful. The room was very clean and the restaurant food was delicious. Overall a great experience in an exciting city.
Reviewed on Aug 11, 2026
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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
Aug 31 - Sep 1
Total with taxes and fees
8.2/10 Very Good! (882 reviews)
"The property was well maintained with comfortable bedding. The breakfast was good and the personnel kept the food well stocked."
Reviewed on Aug 9, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
$122 nightly
$138 total
Aug 27 - Aug 28
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
"Absolutely one of the best hotels I’ve stayed at. Quiet, clean, spacious rooms, beds were very comfortable. Offers in- room dining that is very fast. Parking was easy and the location is great. I’ll definitely stay here again."
Reviewed on Aug 11, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
$96 nightly
$107 total
Aug 16 - Aug 17
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 $450 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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- Winchester Vacations
- Valerie Hill Winery
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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.
