Deals on vacations and trips to Old Town Winchester

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Old Town Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Price was $895, price is now $353 per person
$353
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This smoke-free hotel features a full-service spa, a marina, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $922, price is now $565 per person
$565
per person
May 4 - May 10
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Washington (DCA)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Save 100% on your flight
Price was $849, price is now $535 per person
$535
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a snack bar/deli, and luggage storage are also offered.
Rosewood Washington, D.C.

Rosewood Washington, D.C.

5 out of 5
Northwest
Save 100% on your flight
Price was $1,823, price is now $1,216 per person
$1,216
per person
Mar 31 - Apr 3
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Washington (DCA)
The aparthotel's outdoor pool, indoor pool, and 2 bars/lounges are among the featured amenities. Families will appreciate complimentary bicycles and in-room childcare. Enjoy the 24-hour gym and perks like free WiFi.
Club Wyndham National Harbor

Club Wyndham National Harbor

3.5 out of 5
Save 100% on your flight
Price was $1,894, price is now $1,267 per person
$1,267
per person
May 4 - May 10
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Washington (DCA)
2 hot tubs, an indoor pool, and a 24-hour gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the seasonal outdoor pool and perks like free WiFi.

Top Old Town Winchester hotels deals

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
$127 nightly
The price is $143 total per night
$143 total
Feb 16 - Feb 17
Total with taxes and fees
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.
Pool
Spa
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
$98 nightly
The price is $107 total per night
$107 total
Feb 15 - Feb 16
Total with taxes and fees
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.
Pool
Breakfast included
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $76 total per night
$76 total
Feb 11 - Feb 12
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. There's express check-out and multilingual staff can provide around-the-clock assistance.
Pet friendly
Parking included
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $92 total per night
$92 total
Feb 15 - Feb 16
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
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $92 total per night
$92 total
Feb 16 - Feb 17
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. Free WiFi in public areas, a picnic area, and a computer station are also on offer.
Pool
Breakfast included
TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal

3 out of 5
5 Caroline Drive Front Royal VA
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $128 total per night
$128 total
Feb 15 - Feb 16
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 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.

Popular places to visit

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.

Shenandoah Valley Discovery Museum

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.

Bright Box Theater

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.

Handley Regional Library

Frequently asked questions

How much are vacation packages to Old Town Winchester?
Your travel dreams can all come true in Old Town Winchester from just $353. Our vacation packages include flights and hotels, and they'll make your booking a piece of cake. The only thing you'll need to focus on is what amazing attraction you'll head to first.
Where can I get the best vacation package deals for Old Town Winchester?
No matter how you like to travel, Travelocity can help you get your hands on the perfect Old Town Winchester package deal. All you have to do is pick and choose between our 400 airlines and 1,000,000 properties across the globe.
Why should I book my Old Town Winchester vacation bundle with Travelocity?
Savings, support and a stress-free booking are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you have access to our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you know you'll always get the best deal available.
Can I save money on my Old Town Winchester car rental if I bundle it with a hotel or flight?
Booking an Old Town Winchester vacation package with Travelocity is a surefire way to save you money. You can pick a hotel, car and flight, or any combination of them, and score great discounts. It's also possible to throw in activities and experiences. After you've collected the keys to the rental car, head out of the neighborhood and see what this place has to offer. Roughly 65 mi from Old Town Winchester, White House is certainly worth a road trip.
What is there to do in Old Town Winchester?
While exploring Old Town Winchester, don't forget to check out Shenandoah Valley Discovery Museum and Old Court House Civil War Museum. You won't be bored here!

Photos of local treasures

Browse Old Town Winchester vacation photos for more inspiration

The Courthouse in Winchester, Virginia.
The Courthouse in Winchester, Virginia.
Handley Library
A nice 3 block outdoor downtown shopping area with dining and bars also.
Holiday shopping in Winchester.