Stephens City Vacations from $257

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Price was $372, price is now $257 per person
$257
per person
Dec 25 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,016 reviews)
Everyone was very helpful and engaging.

Reviewed on Oct 30, 2026

Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Save 100% on your flight
Price was $997, price is now $666 per person
$666
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,001 reviews)

Harbor free indoor parking

Harbor free indoor parking

4 out of 5
Downtown Baltimore
Price was $711, price is now $488 per person
$488
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
No reviews

Club Wyndham National Harbor

Club Wyndham National Harbor

3.5 out of 5
Price was $903, price is now $645 per person
$645
per person
Dec 16 - Dec 21
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (504 reviews)
Everything about this hotel was great.

Reviewed on Oct 23, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $543, price is now $394 per person
$394
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,285 reviews)

Don't see what you're looking for?
See all available trips from Columbus to Stephens City
View all trips

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
$83 nightly
The price is $92 total per night from Nov 29 to Nov 30
$92 total
Nov 29 - Nov 30
Total with taxes and fees
Holiday Inn Express Winchester South-Stephens City by IHG
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $78 total per night from Nov 1 to Nov 2
$78 total
Nov 1 - Nov 2
Total with taxes and fees
8.6/10 Excellent! (1,091 reviews)
"The place needs to be redone."

Reviewed on Oct 29, 2026

Travelodge by Wyndham Winchester
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
$130 nightly
The price is $148 total per night from Nov 8 to Nov 9
$148 total
Nov 8 - Nov 9
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel
See all 963 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Stephens City vacation package cost?
Offering excellent value package deals from $257 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.