Stephens City Vacation Packages

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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.

Top Stephens City Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel White House, Washington DC

Club Quarters Hotel White House, Washington DC

3 out of 5
Downtown Washington D.C.
Price was CA $1,126, price is now CA $797 per person
CA $797
per person
Jan 13 - Jan 20
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (2,122 reviews)
The location was perfect. Near the metro and the White House/National monuments. We found reasonable parking about a 5 minute walk on K street. The water station on our floor was very convenient. Staff was friendly and helpful. Will definitely stay here again when in DC.

Reviewed on Nov 1, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was CA $2,004, price is now CA $1,098 per person
CA $1,098
per person
Jan 13 - Jan 20
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,285 reviews)
Just enough

Reviewed on Nov 2, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was CA $1,607, price is now CA $1,156 per person
CA $1,156
per person
Jan 13 - Jan 20
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
8.6/10 Excellent! (1,007 reviews)
The room was clean and spacious. The bed was very comfortable. The location was convenient and close to everything we wanted to see.

Reviewed on Nov 1, 2026

Hilton Club The District Washington D.C.

Hilton Club The District Washington D.C.

3.5 out of 5
Downtown Washington D.C.
Price was CA $1,501, price is now CA $1,090 per person
CA $1,090
per person
Jan 13 - Jan 20
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (672 reviews)
I enjoyed my stay at the Hilton. The rooms were clean and the staff was friendly. It's centrally located and the area was safe. The only down fall is $70.00 a night for parking. We were blessed to be able to park on the street for our weekend stay. The fee for parking is the only negative. I would recommend this hotel.

Reviewed on Nov 2, 2026

Harbor free indoor parking

Harbor free indoor parking

4 out of 5
Downtown Baltimore
Price was CA $1,913, price is now CA $1,390 per person
CA $1,390
per person
Jan 13 - Jan 20
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
No reviews

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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 $115 per night from Nov 7 to Nov 8
CA $115
CA $128 total
Nov 7 - Nov 8
includes taxes & 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
The price is CA $98 per night from Dec 1 to Dec 2
CA $98
CA $108 total
Dec 1 - Dec 2
includes taxes & fees
8.6/10 Excellent! (1,070 reviews)
"Lit et oreillers confortables, par contre le climatiseur ou ventilation de la chambre très bruyant."

Reviewed on Nov 2, 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
The price is CA $182 per night from Nov 9 to Nov 10
CA $182
CA $206 total
Nov 9 - Nov 10
includes taxes & fees
The George Washington Hotel, A Wyndham Grand Hotel
See all 948 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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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.
See properties

Frequently asked questions

How much does a Stephens City vacation package cost?
Offering excellent value package deals from CA $797 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.