Stephens City Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Top Stephens City Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sheraton Baltimore North Hotel
CA $641
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
8.4/10 Very good! (1,003 reviews)
Koi pond. Rooms are renovated. Starbucks. I usually don't feel relaxed in hotels on work trips except in the OC and in Maine... and here. This hotel is up there! Rooms have nice ambience, and Jason working the night shift was great!
Parking in the garage was $20.
Reviewed on Sep 15, 2026
Kellogg Conference Hotel at Gallaudet University
Northeast
CA $681
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
8.4/10 Very good! (1,005 reviews)
It's always a pleasure to stay the Kellogg Hotel and Conference Center.
The staff is always a delight!
Reviewed on Sep 14, 2026
Ready to book your vacation to Stephens City?
Stephens City Hotel Deals
Holiday Inn Express Winchester South-Stephens City by IHG
165 Town Run Ln Stephens City VA
Fully refundable
CA $118
CA $132 total
Sep 20 - Sep 21
includes taxes & fees
8.2/10 Very good! (892 reviews)
"Solo estuve 2 noches. El cuarto tenía olor a humedad aunque se veía limpio. Utilicé lavadora y secadora en las facilidades y funcionaron bien. El desayuno fue muy bueno. Los alrededores estaban limpios y me pareció un área segura. La ubicación es buena pues cuenta con lugares para comer a los que ..."
Reviewed on Sep 10, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
CA $181
CA $206 total
Sep 27 - Sep 28
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Everything was perfect! Highly recommended"
Reviewed on Sep 17, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
CA $96
CA $106 total
Sep 21 - Sep 22
includes taxes & fees
8.6/10 Excellent! (1,074 reviews)
"Better breakfast"
Reviewed on Sep 17, 2026
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.
Stay near popular Stephens City attractions
Valerie Hill Winery
9.6/10 (5 reviews)
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.
Appleland Sports Center
9.0/10 (4 reviews)
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.
Frequently asked questions
How much does a Stephens City vacation package cost?
Offering excellent value package deals from CA $641 on Expedia, you'll be surprised at how little a vacation to Stephens City costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Stephens City?
You're likely to find reduced prices and greater availability in December, January and February. Check out our cheap Stephens City vacation packages and you could get some great off-season discounts.
How many days is enough for Stephens City?
For your Stephens City vacation, a handful of days will be enough to see the top spots. Be sure to stop by The Kernstown Battlefield — it's one of the leading attractions in this destination. If you want more activities, think about basing yourself here and setting off on some day trips from Stephens City.
How to find the best Stephens City package deals?
Use Expedia's handy filters to help you find some great Stephens City package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Stephens City package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Stephens City vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights separately. Better still, you can personalize your Stephens City getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Stephens City?
If you're considering an impromptu Stephens City vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Stephens City?
- Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Stephens City.
- Set a budget: Consider costs such as transportation, flights and meals when working out how much to save for your trip to Stephens City. Then, pick a hotel that fits your budget, whether that's a low-cost option or a more upscale getaway.
- Decide your trip length: Think about how long you want to spend discovering Stephens City. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Bundle your accommodations and airfare: Once you've settled on your dates and duration, lock in the right Stephens City vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
