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.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $349, price is now $246 per person
$246
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
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.
Glover Park Hotel Georgetown

Glover Park Hotel Georgetown

4 out of 5
Northwest
Save 100% on your flight
Price was $684, price is now $440 per person
$440
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
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.
Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $474, price is now $330 per person
$330
per person
Dec 5 - Dec 9
found 14 hours ago
Roundtrip flight included
Dallas (DAL) to Baltimore (BWI)
This apartment features an area shuttle, free self parking, and a free grocery shopping service. Luggage storage and laundry facilities are also provided.
The Graham Georgetown

The Graham Georgetown

4 out of 5
Northwest
Save 100% on your flight
Price was $1,418, price is now $996 per person
$996
per person
Dec 7 - Dec 11
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
This aparthotel features a restaurant and 2 bars/lounges. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a 24-hour business center, and a coffee shop are also offered.
The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,643, price is now $1,188 per person
$1,188
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This luxury hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A library, luggage storage, and laundry facilities are also on offer.

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
Oct 28 - Oct 29
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.
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
$84 nightly
The price is $93 total per night
$93 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $84 total per night
$84 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
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
$85 nightly
The price is $95 total per night
$95 total
Nov 1 - Nov 2
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.
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
$103 nightly
The price is $114 total per night
$114 total
Oct 21 - Oct 22
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.
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
Free Cancellation
$100 nightly
The price is $112 total per night
$112 total
Nov 15 - Nov 16
Total with taxes and fees
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 business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
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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 $246. 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.