Winchester Vacations from $126

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Your Winchester Vacation

From its highlights to its hidden delights, this city is best explored with a Winchester vacation package. Check out hotels located in Mount Vernon, which is great for nightlife, dining and culture. Want to get out and explore? National Aquarium in Baltimore, M&T Bank Stadium and Oriole Park at Camden Yards are just three of the best places to visit during your trip to Winchester. A few quick clicks is all it takes to put together a customized Winchester vacation on Expedia.

The Latest Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Ulysses, a Member of Design Hotels

Hotel Ulysses, a Member of Design Hotels

4 out of 5
Mount Vernon
Save 100% on your flight
Price was $210, price is now $126 per person
$126
per person
Jan 8 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (979 reviews)
I love a good unique stay which is what Ulysses was but it lacked some basic accommodations.. also the parking is super weird and it's crazy that they don't offer valet parking .. I also think it's weird that your not able to control the heat and or air individually in your room

Reviewed on Nov 29, 2025

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 $623, price is now $328 per person
$328
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $1,331, price is now $747 per person
$747
per person
Feb 7 - Feb 14
found 17 hours ago
Roundtrip flight included
Miami (MIA) to Baltimore (BWI)
8.2/10 Very Good! (1,002 reviews)
The staff was outstanding—everyone from the front desk to the room cleaning & maintenance! The campus and environment was also very clean and outstanding. I’ll only stay at Kellogg on my visits to Washington DC!!

Reviewed on Nov 25, 2025

Washington Hilton

Washington Hilton

4 out of 5
Northwest
Price was $968, price is now $570 per person
$570
per person
Feb 19 - Feb 22
found 11 hours ago
Roundtrip flight included
Miami (MIA) to Baltimore (BWI)
8/10 Very Good! (1,002 reviews)
The room, staff, and compliments breakfast were great. Our stay was enjoyable.

Reviewed on Nov 7, 2025

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $223, price is now $135 per person
$135
per person
Jan 8 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (2,362 reviews)
Clean rooms great staff good vibe

Reviewed on Nov 30, 2025

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Where to stay in Winchester

Find the best Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Winchester
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Brooklyn

3/5(657 area reviews)

Shopping, restaurants, and waterfront views are some highlights of Brooklyn. You might stop by Bingo World or Baltimore Inner Harbor Marina while you're in the area.

Find hotels in Brooklyn

Winchester Hotel Deals

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

3 out of 5
1734 W Nursery Rd Linthicum Heights MD
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $77 total per night from Dec 22 to Dec 23
$77 total
Dec 22 - Dec 23
Total with taxes and fees
8/10 Very Good! (4,277 reviews)
We’ve stayed here several times now, and it’s becone our go-to in the area. Convenient, clean, great breakfast. Our only issue (if you can even call it that) is that parking can sometimes be tight. Staff is always amazing. We love it here.

Reviewed on Nov 29, 2025

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

4 out of 5
202 E Pratt St Baltimore MD
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Dec 1 to Dec 2
$179 total
Dec 1 - Dec 2
Total with taxes and fees
8.4/10 Very Good! (2,480 reviews)
Happy hour prices on Friday were great.. $20 for a glass of Meoimi on Saturday was

Reviewed on Nov 23, 2025

Renaissance Baltimore Harborplace Hotel
Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
20 W Baltimore St Baltimore MD
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $96 total per night from Dec 1 to Dec 2
$96 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (2,400 reviews)
Staff interaction is good.

Reviewed on Nov 29, 2025

Lord Baltimore Hotel
See all 1,364 properties in 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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Discover the most popular places to visit in Winchester

Baltimore Inner Harbor Marina

Baltimore Inner Harbor Marina

4.5/5(1,069 reviews)

The transformed former seaport is packed with museums, shops and family attractions and is one of the city’s most photographed areas.

Baltimore Inner Harbor Marina
National Aquarium in Baltimore

National Aquarium in Baltimore

4.5/5(1,044 reviews)

Inner Harbor’s biggest attraction recreates the marine and terrestrial habitats of thousands of animals from many parts of the globe.

National Aquarium in Baltimore
Oriole Park at Camden Yards

Oriole Park at Camden Yards

4.5/5(495 reviews)

Watch Baltimore’s beloved baseball team play on their home field, located inside a groundbreaking stadium famous for blending classic and modern design elements.

Oriole Park at Camden Yards

Things to do

Evening view of the roof top deck on the Spirit of Baltimore cruise vessel

City Cruises Baltimore: Signature Buffet Dinner Cruise with Live DJ & Bars

$133
per adult
84% of travellers recommend
City Cruises Baltimore: Signature Buffet Dinner Cruise with Live DJ & Bars
Two Flight Indoor Skydiving Experience

Two Flight Indoor Skydiving Experience

$96
per traveler
94% of travellers recommend
Two Flight Indoor Skydiving Experience
Glow in the Dark Splatter Paint Experience

Glow in the Dark Splatter Paint Experience

$42
per adult
78% of travellers recommend
Glow in the Dark Splatter Paint Experience
See all activities in Baltimore
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.