Hillsmere Vacations from $304

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Your Hillsmere Vacation

Booking a Hillsmere vacation package is a good way to get to know this neighborhood. From its renowned sites to its lesser-known gems, you won't be short of adventures. Hoping to do some sightseeing during your trip to Hillsmere? Make sure you stop by nearby attractions like Maryland State House, William Paca House and Navy-Marine Corps Memorial Stadium. Don't just imagine it — do it! Reserve your ideal Hillsmere vacation with Expedia and get to where you're going your way.

The Latest Hillsmere Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 out of 5
Price was $403, price is now $304 per person
$304
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
8.2/10 Very Good! (1,016 reviews)
Hotel and rooms need serious work and updating. Breakfast was fine, quick, what expected. Room itself was damp, mixed with a faint smoke odor. Wallpaper peeling, fixtures falling apart, overall not a place we'd stay again. Not a big believer in pet friendly hotels, they tend to smell, which this one did. Sorry

Reviewed on Sep 2, 2025

Hyatt Place Baltimore/Owings Mills

Hyatt Place Baltimore/Owings Mills

3 out of 5
Save 100% on your flight
Price was $500, price is now $325 per person
$325
per person
Oct 24 - Oct 26
found 3 hours ago
Roundtrip flight included
Tampa (TPA) to Baltimore (BWI)
8.2/10 Very Good! (1,105 reviews)
very professional at tge front desk

Reviewed on Sep 5, 2025

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Save 100% on your flight
Price was $715, price is now $484 per person
$484
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,853 reviews)
Great location. Super cool building with historic history.

Reviewed on Sep 6, 2025

Kent Island Resort

Kent Island Resort

3.5 out of 5
Save 100% on your flight
Price was $619, price is now $438 per person
$438
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9.2/10 Wonderful! (111 reviews)
The property overall is charming. Unfortunately the service was just okay. If you’re going to charge me a $30 resort fee, please explain the amenities. Also, the bathroom wasn’t great - old and damaged in spots. We got a deal because we’d stayed mid-week, but even at that, the price seemed too high. Disappointed.

Reviewed on Aug 20, 2025

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Save 100% on your flight
Price was $456, price is now $341 per person
$341
per person
Nov 10 - Nov 14
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,008 reviews)
Excellent service and great staff

Reviewed on Sep 6, 2025

Where to stay in Hillsmere

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

Hillsmere Hotel Deals

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
$158 nightly
The price is $181 total per night from Sep 14 to Sep 15
$181 total
Sep 14 - Sep 15
Total with taxes and fees
Historic Inns of Annapolis
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
9100 Basil Court, Upper Marlboro, MD
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $139 total per night from Sep 29 to Sep 30
$139 total
Sep 29 - Sep 30
Total with taxes and fees
DoubleTree by Hilton Hotel Largo/Washington DC
Aloft BWI Baltimore Washington International Airport

Aloft BWI Baltimore Washington International Airport

3 out of 5
1741 W Nursery Road, Linthicum Heights, MD
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $96 total per night from Sep 14 to Sep 15
$96 total
Sep 14 - Sep 15
Total with taxes and fees
Aloft BWI Baltimore Washington International Airport
See all 1,321 properties in Hillsmere
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 Hillsmere

Maryland Quiet Waters Park which includes a garden

Maryland Quiet Waters Park

Stroll along miles of trails through grassy parkland, hardwood forests and riverfront promenades and check out the visitor center at this pretty park.

Maryland Quiet Waters Park
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

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.