Winchester-on-the-Severn Vacations from $233

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Your Winchester-on-the-Severn Vacation

Winchester-on-the-Severn is calling! Whatever type of getaway you have in mind, you can see and experience the best of this neighborhood with a Winchester-on-the-Severn vacation package. Your trip to Winchester-on-the-Severn wouldn't be complete without seeing leading attractions nearby such as U.S. Naval Academy, Maryland State House and William Paca House. No matter what your ideal Winchester-on-the-Severn vacation looks like, you can make it a reality with Expedia.

The Latest Winchester-on-the-Severn 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 11 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
7/10 Good! (1,008 reviews)
Front desk customer service was excellent! I've definitely recommended a boost in your ratings as it appears you have been unfairly rated.

Reviewed on Jun 27, 2025

DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
Save 100% on your flight
per person
Aug 11 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,367 reviews)
Very clean and friendly staff.

Reviewed on Jul 8, 2025

Element Arundel Mills BWI Airport

Element Arundel Mills BWI Airport

3 out of 5
Save 100% on your flight
per person
Aug 11 - Aug 17
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

Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Inner Harbor
Save 100% on your flight
per person
Aug 11 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (573 reviews)
The hotel was nice I wish that it had a gym and better pillows but it was overall great.

Reviewed on Jul 5, 2025

Hampton Inn & Suites Baltimore Inner Harbor

Hampton Inn & Suites Baltimore Inner Harbor

2.5 out of 5
Downtown Baltimore
Save 100% on your flight
per person
Aug 11 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,001 reviews)
We had to either pay valet parking of $45 or park in a garage or on the street - no validation. There was no microwave in the room. There was no luggage cart when we arrived and no one could find one. There was a problem with the cereal dispenser - it was stuck. The coffee cup lids were really hard to get on - I feared I was going to burn myself trying to get it on. The nice lady at the counter helped me out. The swimming pool was drained for cleaning so we had to wait for that. It wasn’t a bad stay - just a bunch of little things went wrong for one night. The beds were very comfortable!

Reviewed on Jul 8, 2025

Where to stay in Winchester-on-the-Severn

Find the best Winchester-on-the-Severn areas and neighborhoods for the activities you enjoy most. Learn more about Winchester-on-the-Severn
Annapolis which includes street scenes and a city as well as a small group of people

Historic District

1 out of top 10 points of interest in this area
5/5(83 area reviews)

Discover a well-preserved historic district with elements of the original town plan, featuring landmarks like the Maryland State House, St. Ann's Church, and Paca House and Gardens. The neighborhood features prestigious educational institutions like St. John's College and the U.S. Naval Academy.

Find hotels in Historic District

Winchester-on-the-Severn 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
$87 nightly
The price is $99 total per night from Jul 29 to Jul 30
$99 total
Jul 29 - Jul 30
Total includes taxes and fees
8/10 Very Good! (3,759 reviews)
"Everything was nice and clean. Good experience"

Reviewed on Jul 8, 2025

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $163 total per night from Jul 21 to Jul 22
$163 total
Jul 21 - Jul 22
Total includes taxes and fees
8.8/10 Excellent! (1,795 reviews)
THE INN PLACE TO BE
"A quick overnight to celebrate July 4th in Annapolis. The Inn was perfectly placed to take it all in. Easy valet parking; warm, welcoming front desk staff; and, a clean, comfy, well-appointed room made for a memorable holiday."

Reviewed on Jul 5, 2025

Historic Inns of Annapolis
Sonesta ES Suites Baltimore BWI Airport
Sonesta ES Suites Baltimore BWI Airport
3 out of 5
1160 Winterson Rd, Linthicum Heights, MD
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $113 total per night from Aug 3 to Aug 4
$113 total
Aug 3 - Aug 4
Total includes taxes and fees
8/10 Very Good! (1,010 reviews)
"The pool"

Reviewed on Jul 7, 2025

Sonesta ES Suites Baltimore BWI Airport
See all 1,264 properties in Winchester-on-the-Severn
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-on-the-Severn

U.S. Naval Academy which includes military items, interior views and heritage architecture

U.S. Naval Academy

4.5/5(446 reviews)

See where future generations of Navy and Marine Corps officers are trained at this historic federal service academy within a former fort in Annapolis harbor.

U.S. Naval Academy
Chesapeake Bay Bridge

Chesapeake Bay Bridge

4/5(270 reviews)

Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.

Chesapeake Bay Bridge
Sandy Point State Park

Sandy Point State Park

4.5/5(13 reviews)

Sunbathe on the beach, enjoy unrivaled views of the Chesapeake Bay Bridge and go hiking, swimming, fishing and boating in this vast park.

Sandy Point State Park

Things to do

Food Tour Plate

Historic Annapolis Food Tour

$80
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

$32
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

$30
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Annapolis
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.