Old Town Winchester Vacations from $231
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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.
The Churchill Hotel near Embassy Row
Northwest
Save 100% on your flight
Price was $378, price is now $231 per person
$231
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,006 reviews)
Nice location with friendly staff. The hotel is a bit dated and the rooms were too dark for my taste. The fitness center was extremely hot - I had to leave, you cannot adjust the thermostat and the fan is fixed and falling apart. Otherwise the room was large and comfortable, beds were nice, and the bathroom was great, but they could use some anti-slip assistance on the shower floor. Overall I liked it and would stay again.
Reviewed on Jul 10, 2026
Hotel Hive
Northwest
Save 100% on your flight
Price was $473, price is now $263 per person
$263
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (1,514 reviews)
The location of the HIVE is perfect if you are visiting GW. You can park your car, and simply pick it up when you are leaving town. The rooms are small but stylish and simply appointed. Love the overall style of the hotel. Will plan on staying again.
Reviewed on Jul 10, 2026
Lord Baltimore Hotel
Downtown Baltimore
Save 100% on your flight
Price was $664, price is now $384 per person
$384
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (2,841 reviews)
Great service from the front desk when I got to the hotel in the morning, but when I returned late at night, I couldn’t find the television remote in my room and I couldn’t get in touch with the front desk using the room phone.
Reviewed on Jul 11, 2026
Element by Marriott Arundel Mills BWI Airport
Arundel Mills
Save 100% on your flight
Price was $623, price is now $361 per person
$361
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8/10 Very Good! (1,003 reviews)
Didn’t like that room service wasn’t available during my visit. Other than that the location was perfect!
Reviewed on Jul 5, 2026
DoubleTree by Hilton Baltimore North - Pikesville
Save 100% on your flight
Price was $634, price is now $372 per person
$372
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8/10 Very Good! (1,002 reviews)
Staff wasn’t helpful at all. We asked for a loading cart and had to wait for 30 minutes and still didn’t get it. The room had bugs and we had to go to Target across the street for bug spray and the sheets were stain with black crust or something. And they also had a wedding there that made it very unpleasant due to the wedding party was very loud and rude.
Reviewed on Jul 8, 2026
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $138 total per night from Jul 19 to Jul 20
$138 total
Jul 19 - Jul 20
Total with taxes and fees
9.4/10 Exceptional! (1,015 reviews)
"Very good restaurant and staff. Highly recommend This hotel it's very old but up to date,large well furnished rooms and great bed."
Reviewed on Jul 8, 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Jul 26 to Jul 27
$90 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (1,026 reviews)
"Everything was great except for the fact the shower was terrible. It felt like it took me an hour just to rinse the sham out of my hair because the water was coming out in a slow trickle. It was so bad I thought I would have to just rinse my head under the sink!"
Reviewed on Jul 10, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $73 total per night from Jul 26 to Jul 27
$73 total
Jul 26 - Jul 27
Total with taxes and fees
9/10 Wonderful! (1,010 reviews)
"Great staff, clean rooms and delightful breakfast. I'll be back!"
Reviewed on Jul 5, 2026
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.
Stay near popular Old Town Winchester attractions
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- George Washington's Office
- Shen-Val Farm Market
- Museum of the Shenandoah Valley
- Bright Box Theater
- Rocking S Ranch
- Belle Grove Plantation
- Shenandoah University
- Stonewall Jackson's Headquarters
- Cedar Creek and Belle Grove National Historical Park
- Patsy Cline Historic House
- Holy Cross Abbey
- Watermelon Park Campground
- Abram's Delight
- Virginia River Trips
- Mackintosh Fruit Farm
- Valerie Hill Winery
- Jim Barnett Park
- Dinosaur Land
- Shenandoah Valley Discovery Museum
- Rock Harbor Golf Course
- Berryville Vacations
- Hupp's Hill Civil War Park
- Jackson's Chase Golf Course
- Visit Old Town Winchester
- Veramar Vineyard
- Mt Hebron Cemetery
- Appleland Sports Center
- Visit Winchester
- Nalls Farm Market
- Great Falls Park
- 612 Vineyard
- Winchester Vacations
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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.