Winchester Vacations from $234

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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.
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

3 out of 5
Price was $308, price is now $234 per person
$234
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (3,964 reviews)
Clean and comfortable room. Easy shuttle.

Reviewed on Oct 14, 2025

DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Save 100% on your flight
Price was $436, price is now $306 per person
$306
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,006 reviews)
The breakfast was awesome, i recommend anyone to add it to your stay. The staff goes above and beyond to serve you and the are was always clean. Parking is very easy and accessible, even for handicapped guest. Rooms was very tidy and clean.

Reviewed on Oct 14, 2025

Kent Island Resort

Kent Island Resort

3.5 out of 5
Save 100% on your flight
Price was $571, price is now $402 per person
$402
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9.2/10 Wonderful! (114 reviews)
Great INN super nice staff

Reviewed on Sep 16, 2025

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Price was $463, price is now $341 per person
$341
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9/10 Wonderful! (1,825 reviews)
Old vintage building but tremendous character. Bathrooms were small, but expected in such an old building. Bathrooms are updated though. Area was great, ton of shopping and many restaurants. What a charming town.

Reviewed on Oct 14, 2025

Merriweather Lakehouse, Autograph Collection

Merriweather Lakehouse, Autograph Collection

4 out of 5
Town Center
Save 100% on your flight
Price was $782, price is now $579 per person
$579
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (327 reviews)
Definitely recommend this Hotel . Especially if you’re going to the Merriweather Post Pavilion. Great room, great area , will be back for sure.

Reviewed on Oct 11, 2025

Where to stay in Winchester

Find the best Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Winchester
Top of the World Observation Level showing a city and a bay or harbor

Inner Harbor

2 out of top 10 points of interest in this area

Historic seaport with post-industrial waterfront redevelopment, the Inner Harbor offers attractions like the National Aquarium and Maryland Science Center. Easily walk to stadiums or catch a water taxi to explore nearby areas.

Find hotels in Inner Harbor

Winchester Hotel Deals

Hyatt Regency Baltimore Inner Harbor

Hyatt Regency Baltimore Inner Harbor

4 out of 5
300 Light Street, Baltimore, MD
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $159 total per night from Nov 9 to Nov 10
$159 total
Nov 9 - Nov 10
Total with taxes and fees
8.2/10 Very Good! (1,842 reviews)
"We travel to Baltimore every year the past number of years and stay at a different hotel each time at the Inner Harbour. The Hyatt was excellent with every category of hospitality stays. We think we will stay here every year moving forward."

Reviewed on Oct 13, 2025

Hyatt Regency Baltimore Inner Harbor
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
$77 nightly
The price is $87 total per night from Nov 2 to Nov 3
$87 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (4,042 reviews)
"Shuttle always punctual, room environment comfortable."

Reviewed on Oct 10, 2025

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
Holiday Inn Baltimore BWI Airport by IHG

Holiday Inn Baltimore BWI Airport by IHG

3 out of 5
815 Elkridge Landing Road, Linthicum Heights, MD
Fully refundable
$99 nightly
The price is $113 total per night from Nov 9 to Nov 10
$113 total
Nov 9 - Nov 10
Total with taxes and fees
9/10 Wonderful! (1,029 reviews)
"Great shuttle service, polite staff"

Reviewed on Oct 13, 2025

Holiday Inn Baltimore BWI Airport by IHG
See all 1,343 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Winchester

Oriole Park at Camden Yards

Oriole Park at Camden Yards

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
Baltimore Inner Harbor Marina

Baltimore Inner Harbor Marina

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

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

Things to do

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

Spirit of Baltimore Signature Buffet Dinner Cruise with Live DJ & Bars

$137
per adult
84% of travellers recommend
Spirit of 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
Spirit of Baltimore Lunch Cruise boat

Spirit of Baltimore Signature Lunch Cruise

$91
per adult
Spirit of Baltimore Signature Lunch Cruise
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.