Deals on vacations and trips to Old Town Winchester

Choose two or more items and save on your trip:

Old Town Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Convention center Indoor free parking

Convention center Indoor free parking

4 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $460, price is now $297 per person
$297
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
Luggage storage is available at this apartment. Take advantage of the free self parking.
Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
Price was $611, price is now $382 per person
$382
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
The hotel's 24-hour gym, seasonal outdoor pool, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free WiFi. Self parking, a coffee shop, and dry cleaning are also offered.
Hotel Madera

Hotel Madera

4 out of 5
Downtown Washington D.C.
Price was $604, price is now $396 per person
$396
per person
Jan 7 - Jan 11
found 14 hours 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 express check-out, laundry service, and valet parking. A terrace, limo/town car service, and luggage storage are also on offer.
The River Inn

The River Inn

4 out of 5
Northwest
Price was $610, price is now $401 per person
$401
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This aparthotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. A terrace, a free grocery shopping service, and a lobby fireplace are also on offer.
Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Save 100% on your flight
Price was $546, price is now $364 per person
$364
per person
Jan 14 - Jan 19
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like a free area shuttle.

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
$130 nightly
The price is $148 total per night
$148 total
Nov 8 - Nov 9
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
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
Dec 1 - Dec 2
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
$82 nightly
The price is $92 total per night
$92 total
Nov 22 - Nov 23
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.
Pool
Breakfast included
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
$80 nightly
The price is $89 total per night
$89 total
Nov 8 - Nov 9
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
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 8 - Nov 9
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.
Breakfast included
Pet friendly
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
$108 nightly
The price is $121 total per night
$121 total
Nov 4 - Nov 5
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
Don't see what you're looking for?
See all available properties in Old Town Winchester
View all properties
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 $297. 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.