Old Town Winchester Vacations

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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.
Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Save 100% on your flight
per person
Aug 1 - Aug 4
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.8/10 Excellent! (1,001 reviews)
Excellent choice and location!

Reviewed on May 15, 2024

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Aug 1 - Aug 4
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.8/10 Excellent! (1,994 reviews)
It took 15 of running the water to get hot water for my shower and even though my ac was set at 68 the room temp never got below 71 even after a call to maintenance.

Reviewed on May 14, 2024

Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Aug 1 - Aug 4
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.6/10 Excellent! (1,497 reviews)
It’s periodic foyer was so inviting

Reviewed on May 15, 2024

The Graham Georgetown

The Graham Georgetown

4 out of 5
Georgetown
Save 100% on your flight
per person
Aug 1 - Aug 4
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.8/10 Excellent! (1,321 reviews)
Excellent location, friendly staff, comfortable but small room.

Reviewed on May 14, 2024

Hyatt Place National Harbor

Hyatt Place National Harbor

3 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 23
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.2/10 Wonderful! (1,479 reviews)
It was awesome…wish I could’ve stayed longer!

Reviewed on May 15, 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
Fully refundableReserve now, pay when you stay
The price is $125 per night from Jun 16 to Jun 17
$125
$142 total
includes taxes & fees
Jun 16 - Jun 17
9.2/10 Wonderful! (1,008 reviews)
"No"

Reviewed on May 12, 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 $112 per night from May 19 to May 20
$112
$122 total
includes taxes & fees
May 19 - May 20
8.8/10 Excellent! (1,322 reviews)
"My companions and I were on a five day trip. This was the best hotel we stayed at. Everything was new, modern, and nice. The rooms were quiet and comfortable. The breakfast had lots of great choices. I would have been a little hesitant to walk the neighborhood alone, but there were a lot of restaurants ..."

Reviewed on May 12, 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 $84 per night from May 19 to May 20
$84
$92 total
includes taxes & fees
May 19 - May 20
8.8/10 Excellent! (758 reviews)
"Asked for 1st floor room or room near elevator-got neither"

Reviewed on May 14, 2024

Microtel Inn & Suites by Wyndham Winchester
See all 323 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.

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Frequently asked questions

How much does an Old Town Winchester vacation package cost?
Our Old Town Winchester vacation packages, which begin from just $328, 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

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