Winchester-on-the-Severn Vacations from $278

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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.
DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Save 100% on your flight
Price was $474, price is now $278 per person
$278
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)
Bed was super comfy. Restaurant was good. Friendly staff. Clean.

Reviewed on Oct 10, 2025

Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Inner Harbor
Save 100% on your flight
Price was $433, price is now $295 per person
$295
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (741 reviews)
Very nice hotel close to all major tourist destinations. Spacious rooms. Not enough staff in the breakfast room. One person (who did a great job) had no help.

Reviewed on Oct 12, 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
Price was $442, price is now $311 per person
$311
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,013 reviews)
Staff at the front desk were great, however valet workers stole items from our console which was very disappointing. Facility was good.

Reviewed on Oct 13, 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 5 hours 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

Metro Points Hotel

Metro Points Hotel

3 out of 5
Save 100% on your flight
Price was $552, price is now $400 per person
$400
per person
Dec 22 - Dec 29
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
7.4/10 Good! (1,383 reviews)
The place is under renovation. Location is ok.

Reviewed on Sep 26, 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
$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
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
$145 nightly
The price is $166 total per night from Nov 2 to Nov 3
$166 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,846 reviews)
"Quaint historic inn centrally located in the heart of Annapolis. Room was spacious and comfortable. Staff was very friendly."

Reviewed on Oct 10, 2025

Historic Inns of Annapolis
See all 1,299 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

Costa Rica Rainforest Guided Tram Tour

AERIAL TRAM TOUR - HALF DAY PASS Rainforest Adventures Jacó

$67
per adult
AERIAL TRAM TOUR - HALF DAY PASS Rainforest Adventures Jacó
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

$40
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

$26
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
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.