Winchester Vacations from $303

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
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.

The Westin DC Downtown

Downtown Washington D.C.

Save 100% on your flight

$303

per person

Oct 24 - Oct 26

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.8/10 Excellent! (1,003 reviews)

Quick and efficient check in and check out. Excellent location and rooms were very comfortable. We would stay here again!

Reviewed on Sep 21, 2026

Comfort Inn & Suites Baltimore Inner Harbor

Downtown Baltimore

Save 100% on your flight

$361

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

5.2/10 (1,000 reviews)

The Georgetown Inn

Northwest

Save 100% on your flight

$523

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.2/10 Wonderful! (1,009 reviews)

This was a lovely hotel! Close to some shopping and eateries. What a great place to stay!

Reviewed on Sep 21, 2026

Eden Park Guest House

Save 100% on your flight

$336

per person

Nov 23 - Nov 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

7.8/10 Good! (167 reviews)

Eurostars Saint Gregory Dupont Circle Georgetown

Downtown Washington D.C.

Save 100% on your flight

$491

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.8/10 Excellent! (1,009 reviews)

Where to stay in Winchester

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

A cityscape with a river, modern buildings, and a bridge.

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.

A grand library with multiple floors of bookshelves, ornate railings, and a central aisle.

Downtown Baltimore

1 out of top 10 points of interest in this area

Central business district meets historic charm in this neighborhood, with attractions like the National Aquarium, Maryland Science Center, and Lexington Market. Enjoy diverse dining, nightlife, and easy access to public transportation.

A narrow alleyway flanked by brick buildings with ivy, leading to a body of water.

Fells Point

Historic waterfront neighborhood with a maritime vibe, Fell's Point boasts a high concentration of pubs and restaurants. Explore diverse architecture, unique shops, and reach it easily via water taxi or a short walk from the Inner Harbor.

A large stately building with a prominent central tower, surrounded by lush green lawns and trees.

Timonium

If you're looking for some top things to see and do in Timonium and surrounding area, you can visit Towson Town Center and Greenspring Station.

Middle East

Though Middle East might not have many top sights, you can venture to the surrounding area to see attractions like Baltimore Inner Harbor Marina and National Great Blacks in Wax Museum.

Winchester Hotel Deals

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

1734 W Nursery Rd Linthicum Heights MD

Fully refundableReserve now, pay when you stay

$73 nightly

$83 total

Sep 27 - Sep 28

Total with taxes and fees

8.2/10 Very Good! (4,783 reviews)

"Parking was included"

Reviewed on Sep 22, 2026

Renaissance Baltimore Harborplace Hotel

202 E Pratt St Baltimore MD

Fully refundableReserve now, pay when you stay

$188 nightly

$221 total

Oct 8 - Oct 9

Total with taxes and fees

8.4/10 Very Good! (2,513 reviews)

"Awesome"

Reviewed on Sep 22, 2026

Hyatt Regency Baltimore Inner Harbor

300 Light Street Baltimore MD

Fully refundableReserve now, pay when you stay

$195 nightly

$229 total

Oct 1 - Oct 2

Total with taxes and fees

See all 1,366 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.