Book Exclusive Stephens City Vacation Packages

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Stephens City flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
The Waypoint

The Waypoint

2 out of 5
West Rehoboth
Price was CA $1,370, price is now CA $1,035 per person
CA $1,035
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Stay at this hotel in Rehoboth Beach. Enjoy free WiFi, free parking, and a beach shuttle (surcharge). Popular attractions Rehoboth Beach Boardwalk and Rehoboth Beach are located nearby.
The Beacon at Embassy Row, WorldHotels Distinctive

The Beacon at Embassy Row, WorldHotels Distinctive

3.5 out of 5
Downtown Washington D.C.
Price was CA $2,275, price is now CA $1,431 per person
CA $1,431
per person
Oct 11 - Oct 17
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Capital One Arena are located nearby.
Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Price was CA $1,857, price is now CA $1,319 per person
CA $1,319
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
Book a stay at this luxury hotel in Baltimore. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Baltimore Inner Harbor Marina and Oriole Park at Camden Yards are located nearby.
American Guest House

American Guest House

3.5 out of 5
Northwest
Price was CA $1,737, price is now CA $1,294 per person
CA $1,294
per person
Oct 11 - Oct 17
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this business-friendly B&B in Washington. Enjoy free breakfast, free WiFi, and a 24-hour business center. Popular attractions White House and Capital One Arena are located nearby.
The LINE Hotel DC

The LINE Hotel DC

4.5 out of 5
Northwest
Price was CA $1,803, price is now CA $1,351 per person
CA $1,351
per person
Oct 11 - Oct 17
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions White House and Capital One Arena are located nearby.

Top Stephens City hotels 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
Free cancellation
Reserve now, pay when you stay
The price is CA $109 per night
CA $109
CA $122 total
Sep 13 - Sep 14
includes taxes & fees
Book a stay at this business-friendly hotel in Stephens City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Appleland Sports Center and Valerie Hill Winery are located nearby.
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Free cancellation
Reserve now, pay when you stay
The price is CA $106 per night
CA $106
CA $121 total
Sep 28 - Sep 29
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Abram's Delight and Apple Blossom Mall are located nearby.
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
Free cancellation
Reserve now, pay when you stay
The price is CA $180 per night
CA $180
CA $204 total
Sep 17 - Sep 18
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Court House Civil War Museum and Bright Box Theater are located nearby.
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
Free cancellation
The price is CA $142 per night
CA $142
CA $162 total
Oct 11 - Oct 12
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Apple Blossom Mall and Abram's Delight are located nearby.
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Free cancellation
Reserve now, pay when you stay
The price is CA $129 per night
CA $129
CA $143 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Rutherford Crossing and Northside Station Shopping Center are located nearby.
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
Free cancellation
Reserve now, pay when you stay
The price is CA $157 per night
CA $157
CA $175 total
Sep 13 - Sep 14
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Apple Blossom Mall and R-C Track are located nearby.
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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.
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Stephens City Vacations

Ready for your next big adventure? Make sure you don't miss out on any fun in Stephens City by brushing up on one or two things about it before you hurry off.

You'll find this Winchester neighborhood 7 miles (11 kilometers) south of the center of the city.

At last count, the population of Winchester was 26,000.

Hotels in Stephens City

Who doesn't like to be in the heart of the action? Look up our 2 accommodations within easy reach of central Stephens City and start arranging your must-see list for this attractive neighborhood.

Compare the deals and amenities at the Holiday Inn Express Winchester South-Stephens City (165 Town Run Ln) and the  Comfort Inn Stephens City-Winchester South (167 Town Run Ln). These comfortable accommodations are favored by many travelers.

Places to visit in Stephens City

Nothing rivals getting out into nature, and the wider Winchester region has some sensational outdoor activities to try. How about a little hiking? Once you've crossed that off your list, create more special vacation memories by going caving.

Where do you fly into for Stephens City?

Landing at Washington Dulles International Airport (IAD)? Stephens City is only 40 miles (64 kilometers) away. Grab some snacks, hail down a cab and you'll arrive in no time!

Frequently asked questions

How much are vacation packages to Stephens City?
Vacation packages, which provide both flights and hotels in Stephens City, are priced from as little as CA $1,035. Make your travel fantasies come to life and begin your booking with Travelocity today.
How long should my Stephens City vacation be?
Most people book their hotel for 2 nights in Stephens City. But that doesn't mean you have to. How long you spend here boils down to what sorts of things you want to do during your vacation. If you intend to get familiar with every corner of this fantastic place, treat yourself to another night or two (or even longer!).
Where can I get the best vacation package deals for Stephens City?
You'll find a tempting selection of Stephens City package deals on Travelocity. With no less than 400 air carriers and 1,000,000 worldwide properties, piecing together a dream getaway will be simple.
Why should I book my Stephens City vacation bundle via Travelocity?
By booking your flights, hotel, activities and car rental all in one place, you'll save both time and money. We have round-the-clock customer support, and you'll know that you'll always be getting the best deal in town with our Price Match Guarantee. So, what are you waiting for? Book the getaway of your dreams today and start packing!
Will I save money on my Stephens City car rental if I book it with my hotel or flight?
With a Stephens City vacation package, you can bundle your flight, hotel and car bookings and save tons. When you're ready to discover the best of this awesome area, why not start with White House? This renowned attraction is 105 kilometers from Stephens City. With your own wheels, you'll be there before you know it.
Which airport is best for Stephens City?
Stephens City has a couple of major airports to jet into — Washington Dulles Intl. Airport (IAD) (64 kilometers away from the city center) and Hagerstown Regional Airport (HGR) (80 kilometers away from central Stephens City).
What is there to do in Stephens City?
You'll sense a particular magic in the air as you stroll through the streets of Stephens City. Appleland Sports Center and Valerie Hill Winery are just a couple of highlights that make this city such a sought-after destination, so put them on your list of places to see.
Where should I stay when visiting Stephens City?
Many people opt to hit the hay at the Quality Inn Stephens City - Winchester South. It's sure to be a good base for your Stephens City escape.

Photos of local treasures

Browse Stephens City vacation photos for more inspiration

A mountainous landscape with autumn foliage.
A mountainous landscape with dense forests and a valley.
A forested mountain range with autumn foliage.
A forested mountain range with autumn foliage.
A cemetery with brick headstones and a wooden fence.