Old Town Winchester Vacations from $362

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • 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 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 $636, price is now $362 per person
$362
per person
Jul 24 - Jul 29
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

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 $828, price is now $451 per person
$451
per person
Jul 24 - Jul 29
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

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 $694, price is now $408 per person
$408
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (799 reviews)
This hotel is very nice, clean, and the room was large.

Reviewed on May 16, 2026

Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

5 out of 5
Northwest
Save 100% on your flight
Price was $1,130, price is now $667 per person
$667
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,004 reviews)
If you're looking at this hotel, go ahead and book it! Not only is it luxurious and friendly, but you'll find at least 5 taxis by it at any time (a definite plus when certain Metro lines are being repaired). Added bonus: the signature house fragrance is unspeakably delicious. You will love your stay here!

Reviewed on Apr 29, 2026

Hotel Hive

Hotel Hive

3.5 out of 5
Northwest
Save 100% on your flight
Price was $617, price is now $378 per person
$378
per person
Jul 24 - Jul 29
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
The price is $138 total per night from May 25 to May 26
$138 total
per night
May 25 - May 26
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
The price is $87 total per night from May 31 to Jun 1
$87 total
per night
May 31 - Jun 1
9/10 Wonderful! (1,015 reviews)
Everything was great from check-in to checkout. Facilities were clean, room was clean, pool was clean and well taken care bo complaints.

Reviewed on May 16, 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
The price is $77 total per night from May 24 to May 25
$77 total
per night
May 24 - May 25
8.6/10 Excellent! (1,072 reviews)
The room was clean, and the staff was very welcoming and friendly. The location is especially convenient for truckers or anyone needing a quick overnight stop. The rooms have been partially updated with new flooring and a more modern look, but the walls still need some attention, which made the updates ...

Reviewed on May 16, 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.
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

Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

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

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

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

Explore a world of travel with Expedia

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