Old Town Winchester Vacation Packages from $461

Old Town Winchester flight + hotel vacation packages

Prices and availability subject to change. Additional terms may apply.

Glover Park - Georgetown

Northwest

Save 100% on your flight

per person

Jul 19 - Jul 23

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This aparthotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a terrace, and a snack bar/deli are also offered.

Hamilton Hotel Washington DC

Downtown Washington D.C.

Save 100% on your flight

per person

Jul 19 - Jul 23

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, dry cleaning, and luggage storage are also on offer.

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.

Save 100% on your flight

per person

Jul 8 - Jul 15

Roundtrip non-stop flight included

Los Angeles (LAX) to Washington (DCA)

A restaurant and a bar/lounge are featured at this hotel. Families will appreciate the onsite laundry facilities and in-room childcare. WiFi in public areas is free.

Capitol Hill Hotel

Capitol Hill

Save 100% on your flight

per person

Jul 19 - Jul 23

Roundtrip flight included

Boston (BOS) to Washington (DCA)

A gym, valet parking, and laundry facilities are featured at this hotel. Free continental breakfast is served. A business center, a snack bar/deli, and a lobby fireplace are also on offer.

YOTEL Washington DC

Northwest

Save 100% on your flight

per person

Jul 19 - Jul 23

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. You'll appreciate the seasonal outdoor pool, poolside bar, and concierge services.

Top Old Town Winchester hotel deals

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester, VA

Free Cancellation

Reserve now, pay when you stay

$125

per night

May 27 - May 28

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

Hot Tub

Breakfast available

La Quinta Inn & Suites by Wyndham Winchester

1055 Millwood Pike, Route 50 East, Winchester, VA

Free Cancellation

Reserve now, pay when you stay

$108

per night

Apr 28 - Apr 29

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

Pet friendly

Breakfast included

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza, Winchester, VA

Free Cancellation

Reserve now, pay when you stay

$72

per night

May 12 - May 13

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.

Pet friendly

Breakfast included

Travelodge by Wyndham Winchester

160 Front Royal Pike, Winchester, VA

Free Cancellation

Reserve now, pay when you stay

$74

per night

Apr 28 - Apr 29

This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Comfort Inn & Suites

195 Kernstown Commons Blvd, Winchester, VA

Free Cancellation

Reserve now, pay when you stay

$91

per night

May 12 - May 13

This hotel doesn't skimp on freebies - guests receive free self-serve breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Pet friendly

Breakfast included

Ramada by Wyndham Strasburg/Shenandoah Valley

21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA

Free Cancellation

Reserve now, pay when you stay

$81

per night

May 2 - May 3

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. A gym is provided and the front desk is staffed around-the-clock.

Pet friendly

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.

Popular places to visit

Handley Regional Library

5/5(2 reviews)

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.

Shenandoah Valley Discovery Museum

4.5/5(11 reviews)

You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants.

Bright Box Theater

4.5/5(4 reviews)

Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.

Frequently asked questions

How much are vacation packages to Old Town Winchester?

You’ll find an awesome flight + hotel bundle for as low as $461. With a Travelocity vacation package, an escape to Old Town Winchester has never looked so good! Save both time and money and then get a head start on packing those bags.

Where can I get the best vacation package deals for Old Town Winchester?

For the best package deal to Old Town Winchester, you can’t go past Travelocity. Select from 400 air carriers and 1,000,000 properties around the world to create your dream trip — it’s as easy as that.

Why should I book my Old Town Winchester vacation bundle with Travelocity?

Because we believe in crafting special vacation experiences. From flights and hotels to car rentals and activities, our packages make it a breeze to save. Our customer care is available 24/7 to ensure you’re being well taken care of. We also have an amazing Price Match Guarantee, so you can secure your getaway knowing you’ve scored the best deal possible. How? If you find a lower price, we’ll match it!

Can I save on my Old Town Winchester car rental if I combine it with hotels and flights?

Most definitely — and if you also add a tour or an experience to your Old Town Winchester vacation package, you’ll pick up even greater savings. With a package, you can find things to do around the region that suit you. Then, hop in your rental car and work your way through the list. White House is one much-loved sight to check out. You’ll find it 65 mi from Old Town Winchester.

What is the best time of year to go to Old Town Winchester?

July, August and October is high season here, while March, November and December are usually quieter. If your bank balance is your first consideration, avoid traveling in as it tends to be the most expensive time. The most affordable month to see this part of the world is .

What is there to do in Old Town Winchester?

Shenandoah Valley Discovery Museum and Bright Box Theater have enthralled many visitors. Tick these attractions off your Old Town Winchester itinerary and discover what the buzz is about.