Old Town Winchester Vacations

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    You can save when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Old Town Winchester Vacation

Book a customized vacation package to Old Town Winchester and experience the charms of this neighborhood from dawn to dusk. From its cafes and history to its unique personality and vibe, there are tons of fabulous reasons to visit Old Town Winchester. Can't wait to get out and see the sights during your trip to Old Town Winchester? Pencil in a visit to nearby attractions such as Shenandoah University, Rock Harbor Golf Course and Museum of the Shenandoah Valley. Stop daydreaming and start doing. When you're ready to lock in your vacation to Old Town Winchester, Expedia will help get you there.

The Latest Old Town Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
8/10 Very Good! (1,006 reviews)
The cookies were a great bonus. Clean room, terrific shower

Reviewed on 24 May 2024

Kent Island Resort

Kent Island Resort

3.5 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 17
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (68 reviews)
This was a real wedding destination over a resort. Hard to move around when multiple weddings occurring.

Reviewed on 13 May 2024

The Graham Georgetown

The Graham Georgetown

4 out of 5
Georgetown
Save 100% on your flight
per person
Aug 5 - Aug 9
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.8/10 Excellent! (1,335 reviews)
Not only is the location outstanding, but the staff were the most capable and welcoming i encountered in the DC area. It is an easy walk to some very good bakeries and restsurants as well. Close to the Potomac and to Georgetown shopping.

Reviewed on 27 May 2024

Hilton Arlington National Landing

Hilton Arlington National Landing

3.5 out of 5
Crystal City
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9/10 Wonderful! (82 reviews)
Great beds, shuttle to airport was helpful

Reviewed on 1 Jun 2024

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
Jul 11 - Jul 14
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (2,020 reviews)
All necessary things are within walking distance from the hotel

Reviewed on 30 May 2024

Old Town Winchester Hotel 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
The price is CNY906 per night from Jun 16 to Jun 17
CNY906
CNY1,026 total
includes taxes & fees
16 Jun - 17 Jun
9.2/10 Wonderful! (1,002 reviews)
"Wonderful location and very comfortable beds"

Reviewed on 29 May 2024

The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CNY841 per night from Jun 4 to Jun 5
CNY841
CNY915 total
includes taxes & fees
4 Jun - 5 Jun
8.8/10 Excellent! (1,357 reviews)
"Excellent stay"

Reviewed on 29 May 2024

La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
2.5 out of 5
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CNY603 per night from Jun 2 to Jun 3
CNY603
CNY656 total
includes taxes & fees
2 Jun - 3 Jun
8.8/10 Excellent! (789 reviews)
"you can always trust the integrity or this property and facility and the staff!"

Reviewed on 31 May 2024

Microtel Inn & Suites by Wyndham Winchester
See all 314 properties in Old Town Winchester
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Old Town Winchester vacation package cost?
Our Old Town Winchester vacation packages, which begin from just CNY1,520, are the best way to save. All you have to do is choose your preferred hotels, flights and rental car to create your perfect getaway.
How do I get a cheap travel package to Old Town Winchester?
Our Old Town Winchester vacation packages offer plenty of savings for the savvy wanderer. For the best deal, simply bundle your hotel, flights and extras (including activities) into a handy package. But low prices are only the start of your next epic adventure. Book with Expedia and you’ll have more than 550 air carriers and 1,000,000 hotels around the world to pick from. Whatever your budget or style, there’s a package that’s perfect for you.
Where should I stay in Old Town Winchester?
A vacation in Old Town Winchester wouldn’t be complete without checking out Shenandoah University, Winchester Medical Center and Museum of the Shenandoah Valley. Spend your evenings near these tourist attractions and make sightseeing a breeze.
What are the top hotels in Old Town Winchester?
Whether you plan to stay for a night or a week in Old Town Winchester, you’ll get a wonderful night’s rest at The George Washington Hotel, A Wyndham Grand Hotel. This option is a favorite with lots of travelers.
How far in advance should I book my Old Town Winchester vacation?
You’ll be rewarded with the widest variety at the cheapest prices by booking your Old Town Winchester vacation nice and early. Airlines typically advertise tickets anywhere up to 12 months in advance, so start your planning as soon as possible. Having said that, Expedia is constantly working to give you the best bargains around, so there’s never a bad time to book your dream vacation!
What does an Expedia Old Town Winchester travel package include?
Flights, hotels and car rentals — we connect you to all the best deals. All you’ll have to do is decide on your favorite combination. Once you’ve made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it simple to craft an amazing Old Town Winchester getaway.
What should I know before booking an Old Town Winchester travel package?
We already have low prices. However, you’ll enjoy even more bargains when you book your flights, hotels and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and a terrific range of choice.
Can I choose my airline with an Old Town Winchester Expedia vacation package?
With a vacation package, you’re in charge. Whether you’re looking to fly to Old Town Winchester in economy or business class, simply pick from the available airline options. Expedia has access to over 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Old Town Winchester vacation package?
Whether it’s your hotel, flight or rental car, yes, you can cancel or amend it. Booked your Old Town Winchester vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may incur a fee from your hotel, airline or car rental company. For further information, browse our Customer Service Portal. We’re here to help you every step of the way.

Discover the most popular places to visit in Old Town Winchester

Image for Handley Regional Library

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
Image for Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

5/5(19 reviews)

You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Museum of the Shenandoah Valley
Image for Shenandoah Valley Discovery Museum

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

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.