Oyster Harbor Vacations from $225

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Your Oyster Harbor Vacation

Make planning your travels hassle-free by booking a vacation package to Oyster Harbor. We'll take care of the finer points, so you can concentrate on discovering everything this neighborhood can offer. Not sure what to see and do during your trip to Oyster Harbor? Nearby attractions such as Maryland Quiet Waters Park, Annapolis Maritime Museum and Annapolis Landing Marina are great places to start. Stop daydreaming and start doing. When you're ready to lock in your vacation to Oyster Harbor, Expedia will help you get there.

The Latest Oyster Harbor Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Ulysses, a Member of Design Hotels

Hotel Ulysses, a Member of Design Hotels

4 out of 5
Mount Vernon
Save 100% on your flight
Price was $386, price is now $225 per person
$225
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (979 reviews)
The hotel itself was good accommodations. Room was clean and well designed. Staff did not accurately communicate how parking worked with the designated lot creating some issues. Lot is isolated about a block away and accessible by a narrow alley.

Reviewed on Dec 3, 2025

EVEN Hotel Rockville - Washington DC Area by IHG

EVEN Hotel Rockville - Washington DC Area by IHG

3.5 out of 5
Save 100% on your flight
Price was $467, price is now $299 per person
$299
per person
Feb 11 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
8.4/10 Very Good! (1,023 reviews)
Very clean and well kept

Reviewed on Nov 30, 2025

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was $374, price is now $240 per person
$240
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,008 reviews)
The staff especially Marcus & Noam, the valet. I hope I spelled that correctly.

Reviewed on Nov 20, 2025

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Save 100% on your flight
Price was $411, price is now $270 per person
$270
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,001 reviews)
We enjoyed our stay. We were comfortable, had a clean room and the staff were courteous and helpful

Reviewed on Dec 5, 2025

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $421, price is now $283 per person
$283
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (2,362 reviews)
I was extremely happy with our stay. Room was clean (you have to request cleaning services if needed) which I preferred as we were only there a short stay. Easy access to anything downtown. 15-20 min walk to M&T Bank Stadium and about 10-15 from the Inner Harbor. The hotel itself is on the older side which I loved. As a history buff this was right up my alley looking at the beautiful Art-Deco elements of the front entrance. The ceiling of the lobby is stunning. My next trip I will definetly be planning to stay here again. As someone who rarely takes the time to write a review, this is worth it.

Reviewed on Dec 4, 2025

Where to stay in Oyster Harbor

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

Historic District

2 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

Oyster Harbor 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
$144 nightly
The price is $164 total per night from Jan 1 to Jan 2
$164 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.8/10 Excellent! (1,910 reviews)
Excellent hotel Really nice staff Love the valet guys

Reviewed on Nov 30, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $144 total per night from Dec 21 to Dec 22
$144 total
Dec 21 - Dec 22
Total with taxes and fees
9.2/10 Wonderful! (1,008 reviews)
Clean rooms, comfortable beds, friendly staff.

Reviewed on Nov 28, 2025

Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $94 total per night from Jan 4 to Jan 5
$94 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Great place!

Reviewed on Dec 3, 2025

DoubleTree by Hilton Hotel Annapolis
See all 1,197 properties in Oyster Harbor
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 Oyster Harbor

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
Phantoms of Annapolis Ghost Tour By US Ghost Adventures

Ashes and Apparitions of Annapolis Ghost Tour

$32
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost 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.