Stephens City Vacation Packages 2026 from $539

Stephens City flight + hotel vacation packages

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

Holiday Inn National Airport/Crystal City by IHG

Crystal City

Save 100% on your flight

$539

per person

Sep 12 - Sep 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

This smoke-free hotel features 2 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. A free area shuttle is offered as well.

The Westin Annapolis

Save 100% on your flight

$677

per person

Sep 18 - Sep 22

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Baltimore (BWI)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this Beaux Arts hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and snack bar/deli.

Historic Inns of Annapolis

Historic District

Save 100% on your flight

$634

per person

Sep 18 - Sep 22

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Baltimore (BWI)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A terrace, limo/town car service, and a garden are also on offer.

Hotel Burg

Leesburg's Old and Historic District

Save 100% on your flight

$1,034

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and a terrace are also offered.

DoubleTree by Hilton Hotel Annapolis

Save 100% on your flight

$566

per person

Sep 18 - Sep 22

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Baltimore (BWI)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.

Top Stephens City hotels deals

Holiday Inn Express Winchester South-Stephens City by IHG

165 Town Run Ln Stephens City VA

Free Cancellation

$87 nightly

$97 total

Jul 14 - Jul 15

Total with taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$90 total

Jul 26 - Jul 27

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

Free Cancellation

Reserve now, pay when you stay

$69 nightly

$79 total

Jul 26 - Jul 27

Total with taxes and fees

The hotel doesn't skimp on freebies - guests receive free continental breakfast and free self parking. Traveling for business? Take advantage of the business center, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike Winchester VA

Free Cancellation

$90 nightly

$100 total

Aug 2 - Aug 3

Total with taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Parking included

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$138 total

Jul 16 - Jul 17

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this Georgian hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.

Pool

Spa

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$102 total

Jul 26 - Jul 27

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

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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.

See properties

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 $539. 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 65 mi 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) (40 mi away from the city center) and Hagerstown Regional Airport (HGR) (50 mi 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.