Stephens City Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Stephanie Sutton

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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.

Top Stephens City Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8/10 Very Good! (968 reviews)
Acceptable for my one night stay

Reviewed on Aug. 8, 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Washington (DCA)
8.6/10 Excellent! (1,005 reviews)
My stay was very pleasant

Reviewed on Jul. 27, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Washington (DCA)
9.8/10 Exceptional! (28 reviews)
Absolutely incredible hotel that we happened upon on a whim. Brand new, absolutely stunning and Johnny the concierge made our night and had us feeling right at home despite the grandeur of the establishment. Can’t recommend this place enough and shout out to Johnny ❤️

Reviewed on Aug. 3, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (WAS)
8.2/10 Very Good! (1,007 reviews)
Beautiful facility inside Galludet University. Allowable price and free parking in the middle of Washington DC. Thoroughly enjoyed my stay. The room was large and had many amenities. My stay was quiet and peaceful. I will definitely be back!

Reviewed on Jul. 21, 2025

Rosewood Washington, D.C.

Rosewood Washington, D.C.

5 out of 5
Northwest
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (WAS)
9.2/10 Wonderful! (187 reviews)
Enjoyed my stay here. Our room was spacious. The staff were friendly. A lovely staff member named Abrehet was most especially helpful, and accommodating! Will be back.

Reviewed on Jul. 8, 2025

Ready to book your vacation to Stephens City?

 

Choose your dates

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
The price is CA $114 per night from Aug 22 to Aug 23
CA $114
CA $124 total
Aug 22 - Aug 23
includes taxes & fees
8.2/10 Very Good! (762 reviews)
"Its so convenient. Right off of 81. The staff is excellent as is the facility."

Reviewed on Jul. 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
The price is CA $133 per night from Sep 7 to Sep 8
CA $133
CA $145 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (2,113 reviews)
"Safe easy exercise from interstate"

Reviewed on Aug. 4, 2025

La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $109 per night from Sep 1 to Sep 2
CA $109
CA $118 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,323 reviews)
"Only thing I would change is the shower no pressure in room 309"

Reviewed on Aug. 3, 2025

Microtel 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Stephens City

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

Frequently asked questions

How much does a Stephens City vacation package cost?
Offering excellent value package deals from CA $524 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.