Stephens City Vacations from $341

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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

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $503, price is now $341 per person
$341
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (3,027 reviews)
Loved it. Great location and the lobby is beautiful

Reviewed on Jul 28, 2026

The Poppy Georgetown

The Poppy Georgetown

4 out of 5
Northwest
Price was $3,015, price is now $1,683 per person
$1,683
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
9.4/10 Exceptional! (588 reviews)

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $1,617, price is now $948 per person
$948
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9.6/10 Exceptional! (97 reviews)

Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
Save 100% on your flight
Price was $935, price is now $606 per person
$606
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (2,197 reviews)
The best hotel I ever stayed. I want to come back whenever I travel to DC again. It's so convenient to get train station. Recommended to my friends.

Reviewed on Jul 28, 2026

Eden Park Guest House

Eden Park Guest House

3.5 out of 5
Save 100% on your flight
Price was $690, price is now $466 per person
$466
per person
Oct 10 - Oct 17
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
7.8/10 Good! (166 reviews)

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Stay 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.
See properties

Stephens City Hotel Deals

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 out of 5
165 Town Run Ln Stephens City VA
Fully refundable
$77 nightly
The price is $86 total per night from Aug 23 to Aug 24
$86 total
Aug 23 - Aug 24
Total with taxes and fees
8.2/10 Very Good! (877 reviews)
"Hotel room and bathroom dated. Breakfast on weekend had more options that weren’t available during the week such as fruit and oatmeal. There was communal half and half in unmarked container. I’ve stayed at other Holiday Inn’s and did not see this. Parking was difficult at times and spots were ..."

Reviewed on Jul 27, 2026

Holiday Inn Express Winchester South-Stephens City by IHG
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
$86 nightly
The price is $95 total per night from Aug 9 to Aug 10
$95 total
Aug 9 - Aug 10
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
"Room was decent."

Reviewed on Jul 28, 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 Aug 6 to Aug 7
$138 total
Aug 6 - Aug 7
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
"The 20's decor and authentic details added to classy feel of the hotel. Unique Romanesque pool. 5 minute walk to the Pedestrian Mall."

Reviewed on Jul 28, 2026

The George Washington Hotel, A Wyndham Grand Hotel
See all 902 properties in Stephens City
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 $341 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.