Winchester Vacations from $247

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Days Inn & Suites by Wyndham Laurel Near Fort Meade

Days Inn & Suites by Wyndham Laurel Near Fort Meade

2 out of 5
North Laurel
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
7/10 Good! (1,011 reviews)
Everything was fine

Reviewed on Jul 13, 2025

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
Very close to a lot of entertainment and dining. Staff was friendly and welcoming.

Reviewed on Jul 11, 2025

The William Fell Baltimore, Tapestry Collection by Hilton

The William Fell Baltimore, Tapestry Collection by Hilton

3.5 out of 5
Fells Point
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (37 reviews)
The hotel location was perfect. Close to everything. Shopping, the beautiful water, restaurants, bars, water taxi etc. the staff was wonderful. Krystal was warm and welcoming and everyone always asked how you were and if you needed anything. My only gripe was it was so loud in the room at night. You could hear people’s conversations, cars, the bar music. The tv wasnt even drowning out the noise. But other than that, it was clean, safe and a great place with alot to do. Just dont stay on the city side if you want quiet at night

Reviewed on Jul 12, 2025

DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,354 reviews)
Friendly staff, clean hotel, good food served at hotel restaurant.

Reviewed on Jul 12, 2025

Element Arundel Mills BWI Airport

Element Arundel Mills BWI Airport

3 out of 5
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
Shower was banged up with cracks in wall and handle fell off when I grabbed it.

Reviewed on Jul 8, 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
$161 nightly
The price is $189 total per night from Jul 24 to Jul 25
$189 total
Jul 24 - Jul 25
Total includes taxes and fees
8.2/10 Very Good! (1,702 reviews)
"Great"

Reviewed on Jul 12, 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
$79 nightly
The price is $90 total per night from Jul 20 to Jul 21
$90 total
Jul 20 - Jul 21
Total includes taxes and fees
8/10 Very Good! (3,769 reviews)
"It had a noisy neighbor, but it was not the hotel issue. However, a guard could have a better outcome"

Reviewed on Jul 12, 2025

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
The Royal Sonesta Harbor Court Baltimore
The Royal Sonesta Harbor Court Baltimore
4.5 out of 5
550 Light Street, Baltimore, MD
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $206 total per night from Aug 10 to Aug 11
$206 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (1,516 reviews)
"Great service, clean and comfortable. Great amenities"

Reviewed on Jul 12, 2025

The Royal Sonesta Harbor Court Baltimore
See all 1,339 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

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
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

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

$133
per adult
82% of travellers recommend
Spirit of Baltimore Signature Buffet Dinner Cruise with Live DJ & Bars
Glow in the Dark Splatter Paint Experience

Glow in the Dark Splatter Paint Experience

$35
per child
78% of travellers recommend
Glow in the Dark Splatter Paint Experience
Downtown Baltimore Helicopter Tour

Downtown Baltimore Helicopter Tour

$125
per adult
Downtown Baltimore Helicopter Tour
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.