Old Town Winchester Vacations from $169

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Your Old Town Winchester Vacation

Book a customized vacation package to Old Town Winchester and experience the wonders of this neighborhood from sunup to sundown. From its cafes and history to its distinct personality and vibe, there are loads of good reasons to visit Old Town Winchester. Hoping to sightsee during your trip to Old Town Winchester? Don't miss nearby attractions like Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Stop daydreaming and start doing. When it's time to book your ideal 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.
Home2 Suites By Hilton Ashburn, Va

Home2 Suites By Hilton Ashburn, Va

3 out of 5
Save 100% on your flight
Price was $334, price is now $169 per person
$169
per person
Jan 6 - Jan 10
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
No reviews
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was $1,505, price is now $679 per person
$679
per person
Feb 12 - Feb 17
found 16 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Baltimore (BWI)
8.6/10 Excellent! (1,008 reviews)
The staff especially Marcus & Noam, the valet. I hope I spelled that correctly.

Reviewed on Nov 20, 2025

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 $821, price is now $412 per person
$412
per person
Feb 12 - Feb 16
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,084 reviews)
Great hotel in an excellent location that is close to most museums

Reviewed on Nov 27, 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Save 100% on your flight
Price was $425, price is now $226 per person
$226
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,005 reviews)
Coffee maker didn’t work, restaurant was welcoming and food subpar. Missing robe

Reviewed on Nov 24, 2025

Embassy Suites by Hilton Washington D.C. – Convention Center

Embassy Suites by Hilton Washington D.C. – Convention Center

3.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $977, price is now $538 per person
$538
per person
Feb 12 - Feb 16
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (2,031 reviews)
Wonderful location and hotel

Reviewed on Nov 26, 2025

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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
$127 nightly
The price is $144 total per night from Dec 1 to Dec 2
$144 total
Dec 1 - Dec 2
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
The breakfast was very good. The menu had a lot of options. It came to our table nice and hot! I loved the waffle with Lemon ricotta, syrup and butter. Our waitress always knew when to fill my coffee to keep it warm! Everything was very clean and neatly set up. The waitresses were also cheerful and ...

Reviewed on Nov 20, 2025

The George Washington Hotel, A Wyndham Grand Hotel
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
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $102 total per night from Dec 16 to Dec 17
$102 total
Dec 16 - Dec 17
Total with taxes and fees
9.2/10 Wonderful! (2,230 reviews)
Courteous front desk Pricing good

Reviewed on Nov 25, 2025

La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $74 total per night from Dec 1 to Dec 2
$74 total
Dec 1 - Dec 2
Total with taxes and fees
8.4/10 Very Good! (1,093 reviews)
Clean and comfortable.

Reviewed on Nov 23, 2025

Travelodge by Wyndham Winchester
See all 372 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Old Town Winchester

Staircase at Handley 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 charming coffeehouses or top-notch restaurants in this walkable area.

Handley Regional Library
Gardens at Glen Burnie House.

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 top-notch restaurants or charming coffeehouses in this walkable area.

Museum of the Shenandoah Valley

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.