Old Town Winchester Vacations from $314

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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.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $490, price is now $314 per person
$314
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,001 reviews)
Parking detached from the actual hotel. Location setting is excellent and close to many shops and local

Reviewed on May 12, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,643, price is now $963 per person
$963
per person
Jun 19 - Jun 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,000 reviews)
Unexpected upgrade at check in. Was much appreciated!

Reviewed on May 16, 2026

Kimpton Banneker Hotel by IHG

Kimpton Banneker Hotel by IHG

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $675, price is now $418 per person
$418
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (799 reviews)
We live Kimpton and this is our new favorite. Everything was exceptional, starting with the staff who all could no have been more helpful and accommodating in every interaction. The hotel itself is gorgeous, and the restaurant - oh it was so delicious - special thanks to Helen our server! We were even able to enjoy a cocktail out front in from of the fire pit. Highly recommend!

Reviewed on May 17, 2026

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 $779, price is now $509 per person
$509
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,184 reviews)
The staff was so helpful and great but the beds and pillows were so uncomfortable. The pillows especially were awful and we changed them too. Still bad. Won’t stay there again because we both slept so badly.

Reviewed on May 15, 2026

Hotel Hive

Hotel Hive

3.5 out of 5
Northwest
Save 100% on your flight
Price was $528, price is now $347 per person
$347
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (1,433 reviews)
Lots of useful information

Reviewed on May 16, 2026

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
$122 nightly
The price is $138 total per night from May 25 to May 26
$138 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (1,005 reviews)
You can’t go wrong staying here. The staff were very friendly. The beds were very comfortable and the room was very clean. This hotel is centrally located so you can park your car and walk around the old town area. This was our second time staying here and it didn’t disappoint. We will definitely ...

Reviewed on May 17, 2026

The George Washington Hotel, A Wyndham Grand Hotel
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $87 total per night from May 31 to Jun 1
$87 total
May 31 - Jun 1
Total with taxes and fees
9/10 Wonderful! (1,019 reviews)
Would like to see a bigger breakfast with hot items. The property is very clean and staff are super friendly. This is my third time here and we will be staying again next year.

Reviewed on May 17, 2026

Spark by Hilton 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
$71 nightly
The price is $77 total per night from May 24 to May 25
$77 total
May 24 - May 25
Total with taxes and fees
8.6/10 Excellent! (1,073 reviews)
Comfortable for the 1 night I needed room for

Reviewed on May 17, 2026

Travelodge by Wyndham Winchester
See all 370 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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All Inclusive Vacations
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Beach Vacations
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Kid Friendly Vacations

Discover the most popular places to visit in Old Town Winchester

Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

5/5(20 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
Jim Barnett Park

Jim Barnett Park

4/5(1 review)

Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Jim Barnett Park

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.