Old Town Winchester Vacations from $213

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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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Price was $464, price is now $213 per person
$213
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (1,178 reviews)
The hotel itself is nice. Friendly front desk. Spacious, updated, but a little too heavy on the cleaning products as the smell was overwhelming in the hallway. However, the surrounding area is hit/miss. Not walkable, very congested, definitely need transportation to get around.

Reviewed on Jan 13, 2026

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Price was $970, price is now $319 per person
$319
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,005 reviews)
Clean rooms, great amenities and delicious breakfast

Reviewed on Jan 12, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was $1,065, price is now $550 per person
$550
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,084 reviews)
The place was nice, BUT the hidden charges of Urban Experience charges were a surprise, and of course I was not happy about.

Reviewed on Jan 12, 2026

Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Save 100% on your flight
Price was $776, price is now $452 per person
$452
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,002 reviews)
Room was clean and staff was friendly

Reviewed on Jan 12, 2026

Sonesta Hotel Baltimore Inner Harbor

Sonesta Hotel Baltimore Inner Harbor

4 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $435, price is now $257 per person
$257
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (998 reviews)
Room was clean, staff was fine, location great for Convention Center and the Harbor. Price was great. Will be back next year.

Reviewed on Jan 15, 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
$127 nightly
The price is $143 total per night from Jan 22 to Jan 23
$143 total
Jan 22 - Jan 23
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
Staff was amazing! Benjamin and Carla are two of the kindest people ever!

Reviewed on Jan 4, 2026

The George Washington Hotel, A Wyndham Grand Hotel
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
$82 nightly
The price is $89 total per night from Jan 26 to Jan 27
$89 total
Jan 26 - Jan 27
Total with taxes and fees
9/10 Wonderful! (1,428 reviews)
This is our number one spot to stay in in Winchester. The location is perfect. Rooms are clean and modern.

Reviewed on Jan 14, 2026

Microtel Inn & Suites by Wyndham Winchester
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
$92 nightly
The price is $100 total per night from Jan 18 to Jan 19
$100 total
Jan 18 - Jan 19
Total with taxes and fees
9.2/10 Wonderful! (2,242 reviews)
Clean room; really comfortable bed. Great staff

Reviewed on Jan 8, 2026

La Quinta Inn & Suites by Wyndham Winchester
See all 364 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

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

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

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

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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.