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.
Residence Inn by Marriott Alexandria Old Town South at Carlyle

Residence Inn by Marriott Alexandria Old Town South at Carlyle

3 out of 5
Eisenhower East
Save 100% on your flight
Price was $823, price is now $502 per person
$502
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Club Quarters Hotel White House, Washington DC

Club Quarters Hotel White House, Washington DC

3 out of 5
Downtown Washington D.C.
Price was $1,117, price is now $565 per person
$565
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Baltimore (BWI)
A 24-hour gym is featured at this hotel, along with free WiFi in public areas and a communal living room. Business travelers can take advantage of the business center. Express check-in, express check-out, and a computer station are also on offer.
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,402, price is now $795 per person
$795
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Baltimore (BWI)
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.
Hotel Hive

Hotel Hive

3.5 out of 5
Northwest
Save 100% on your flight
Price was $850, price is now $505 per person
$505
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features a restaurant, a rooftop terrace, and a bar/lounge. WiFi in public areas is free. A terrace and luggage storage are also provided.
Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $1,137, price is now $702 per person
$702
per person
Oct 21 - Oct 25
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) 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.

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
$130 nightly
The price is $148 total per night
$148 total
Sep 17 - Sep 18
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, express check-in, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and concierge services.
Pool
Spa
Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city

Winchester VA
$295 nightly
The price is $334 total per night
$334 total
Sep 15 - Sep 16
Total with taxes and fees
This apartment features laundry facilities.
Kitchen
Washer
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
$77 nightly
The price is $87 total per night
$87 total
Oct 11 - Oct 12
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
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
$93 nightly
The price is $104 total per night
$104 total
Sep 27 - Sep 28
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
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
$106 nightly
The price is $118 total per night
$118 total
Oct 11 - Oct 12
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
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 $77 total per night
$77 total
Sep 13 - Sep 14
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
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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 Old Town Winchester attractions

Shenandoah Valley Discovery Museum

8.6/10 (78 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.
See properties

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 $502. 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

A white neoclassical building with columns, an American flag, and a clock tower.
A building with a green roof and ornate architectural details.
A red brick church with a blue door and a clock tower.
A brick building with a cafe on the ground floor and a church steeple in the background.
A brick-paved street lined with shops and cafes, under a cloudy sky.