Stephens City Vacations from $328

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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.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $485, price is now $328 per person
$328
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,012 reviews)
This is a safe, nice hotel on a college campus in a great location of DC. The staff was friendly and professional. The only thing we had an issue is with allergies. Seemed like a dust issue as the rooms all have the air conditioning with recycled air. Overall great property.

Reviewed on Jun 15, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $1,042, price is now $681 per person
$681
per person
Aug 5 - Aug 11
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.6/10 Exceptional! (72 reviews)
Wonderful short stay. Helpful and fun staff. Loved the valet to the winery.

Reviewed on Jun 13, 2026

Rachael's Inner Harbor Boutique Inn

Rachael's Inner Harbor Boutique Inn

3 out of 5
Ridgely's Delight
Save 100% on your flight
Price was $945, price is now $629 per person
$629
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
10/10 Exceptional! (4 reviews)
Beautiful and spacious

Reviewed on May 21, 2026

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
Price was $492, price is now $330 per person
$330
per person
Jul 16 - Jul 19
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,857 reviews)
I would’ve liked to have the ability to access Netflix.

Reviewed on Jun 14, 2026

Holiday Inn Gaithersburg by IHG

Holiday Inn Gaithersburg by IHG

3.5 out of 5
Save 100% on your flight
Price was $554, price is now $380 per person
$380
per person
Jul 31 - Aug 6
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,000 reviews)
Great stay and experience clean and smooth no bed bugs or fleas

Reviewed on Jun 14, 2026

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Stay near popular Stephens City attractions

Valerie Hill Winery

9.6/5 (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
$100 nightly
The price is $109 total per night from Jun 21 to Jun 22
$109 total
Jun 21 - Jun 22
Total with taxes and fees
8.2/10 Very Good! (859 reviews)
"Terrible experience—avoid this hotel!The pool was closed, and both the lobby and rooms were dirty. The breakfast was gross. To make matters worse, our original toilet didn't flush, forcing us to pack up and change rooms. Disappointing stay.Option 2: Detailed and"

Reviewed on Jun 10, 2026

Holiday Inn Express Winchester South-Stephens City by IHG
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $99 total per night from Jul 6 to Jul 7
$99 total
Jul 6 - Jul 7
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
"Excellent hotel, very clean, nice beds."

Reviewed on Jun 15, 2026

Spark by Hilton Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $76 total per night from Jul 5 to Jul 6
$76 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (958 reviews)
"Excellent value"

Reviewed on Jun 16, 2026

TRU By Hilton Winchester
See all 909 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 $328 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.