Stephens City Vacations from $255

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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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
Price was $448, price is now $255 per person
$255
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8/10 Very Good! (968 reviews)
People camping on the medium strip between highways. Stranger in front of hotel door cornered me and talked for over 30 minutes when all I wanted to do is get in my room and chill.

Reviewed on Aug 18, 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Save 100% on your flight
Price was $1,118, price is now $588 per person
$588
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
9.4/10 Exceptional! (1,012 reviews)
The Wharf is a beautiful area of DC. This hotel is very nice, fancy yet understated. Our room was clean, large and comfortable. Valet parking was a plus. Walkable to great restauranta and to The Anthem. A great concert venue. Our stay was lovely.

Reviewed on Aug 18, 2025

DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Save 100% on your flight
Price was $542, price is now $307 per person
$307
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
This is definitely not four stars facility. More like two and half. Our stay for one night was ok. Sheets were clean. Fridge was missing in the cabinet in our room.

Reviewed on Aug 14, 2025

The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Save 100% on your flight
Price was $1,081, price is now $638 per person
$638
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
this was a well-priced hotel and we found it to be cute and homey- sort of like you were at a beach hotel. Happy vibes:)

Reviewed on Aug 17, 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $739, price is now $469 per person
$469
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8.6/10 Excellent! (1,005 reviews)
Good location, friendly staff, great breakfast, clean and quiet rooms, best sleep in a week

Reviewed on Aug 12, 2025

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Discover the most popular places to visit in Stephens City

Valerie Hill Winery

You can enjoy a tasting or tour at Valerie Hill Winery during your travels to Stephens City. While you're here, you can savor the top-notch restaurants.

Valerie Hill Winery

Appleland Sports Center

You can take time to visit Appleland Sports Center during your travels to Stephens City. While you're here, you can savor the top-notch restaurants.

Appleland Sports Center

Stephens City Hotel Deals

Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South

2.5 out of 5
167 Town Run Ln, Stephens City, VA
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $77 total per night from Sep 15 to Sep 16
$77 total
Sep 15 - Sep 16
Total includes taxes and fees
7.8/10 Good! (600 reviews)
"Very clean. Room animal accepted Front desk pleasent"

Reviewed on Aug 17, 2025

Quality Inn Stephens City - Winchester South
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
$80 nightly
The price is $87 total per night from Sep 10 to Sep 11
$87 total
Sep 10 - Sep 11
Total includes taxes and fees
8.2/10 Very Good! (765 reviews)
"pool was closed. breakfast had issues. out of items. room was nice and clean."

Reviewed on Aug 15, 2025

Holiday Inn Express Winchester South-Stephens City by IHG
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $112 total per night from Sep 1 to Sep 2
$112 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (2,133 reviews)
"Just a suggestion. I am disabled and was placed in a lovely room on the 6th floor. The fire alarm went off and my concern is how is someone in a wheelchair going to evacuate without the elevator. Maybe all ada rooms shou"

Reviewed on Aug 19, 2025

La Quinta Inn & Suites by Wyndham Winchester
See all 874 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.

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Frequently asked questions

How much does a Stephens City vacation package cost?
Offering excellent value package deals from $255 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.