Winchester Vacations from $192

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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.
DoubleTree by Hilton Columbia

DoubleTree by Hilton Columbia

4 out of 5
Oakland Mills
Save 100% on your flight
Price was $280, price is now $192 per person
$192
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,001 reviews)
The staff was wonderful, the lobby is nice, and it is nice to have a restaurant on site. My room was big and clean; the bed was comfortable. However, it's age is starting to show. The heater in the room was so loud and there were huge gaps in the door, so all the heat flowed out, and the heater kept kicking on. I would stay here again.

Reviewed on Jan 14, 2026

Sonesta Hotel Baltimore Inner Harbor

Sonesta Hotel Baltimore Inner Harbor

4 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $434, price is now $269 per person
$269
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)
Clean and spacious room! Service all around was excellent. Would stay again!!!

Reviewed on Jan 12, 2026

Baltimore executive Furnished rentals

Baltimore executive Furnished rentals

4 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $420, price is now $267 per person
$267
per person
Feb 17 - Feb 21
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8/10 Very Good! (2 reviews)
Hyatt House BWI Airport Baltimore

Hyatt House BWI Airport Baltimore

3 out of 5
Save 100% on your flight
Price was $282, price is now $194 per person
$194
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (665 reviews)
Everything was clean and the staff was professional

Reviewed on Jan 11, 2026

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

4 out of 5
Inner Harbor
Save 100% on your flight
Price was $617, price is now $431 per person
$431
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (2,459 reviews)
Elevator was completely out on New Year’s Eve, we were on 11th floor.

Reviewed on Jan 10, 2026

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 Jan 25 to Jan 26
$77 total
Jan 25 - Jan 26
Total with taxes and fees
8/10 Very Good! (4,433 reviews)
Clean room

Reviewed on Jan 13, 2026

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 Jan 18 to Jan 19
$179 total
Jan 18 - Jan 19
Total with taxes and fees
8.4/10 Very Good! (2,533 reviews)
Elevator was completely out on New Year’s Eve, we were on 11th floor.

Reviewed on Jan 10, 2026

Renaissance Baltimore Harborplace Hotel
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 Jan 28 to Jan 29
$159 total
Jan 28 - Jan 29
Total with taxes and fees
8.2/10 Very Good! (1,905 reviews)
.

Reviewed on Jan 11, 2026

Hyatt Regency Baltimore Inner Harbor
See all 1,409 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

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
Homewood Museum which includes a garden, signage and heritage elements

Johns Hopkins University

Enjoy the collegiate vibe at Johns Hopkins University as part of your travels around Baltimore. Amble around this vibrant area's waterfront or attend a sporting event.

Johns Hopkins University

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

$154
per adult
88% 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

$40
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.