Oyster Harbor Vacations from $391

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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.
DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
Price was $497, price is now $391 per person
$391
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,248 reviews)
Very convenient for BWI travel.

Reviewed on Mar 19, 2026

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was $752, price is now $549 per person
$549
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (2,675 reviews)
Other than the gorgeous architecture and beautiful lobby, the place was pretty average. The room was clean, but I was short-sheeted (not funny guys!). Didn't see any ghosts, so I was bummed about that.

Reviewed on Mar 19, 2026

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
Price was $1,072, price is now $825 per person
$825
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Houston (IAH) to Baltimore (BWI)
9.4/10 Exceptional! (1,005 reviews)
The hotel has cute and trendy decor. It’s located centrally nearby many restaurants and coffee shops around. Our room was clean and spacious. Check in was easy and on point. We had no issues with this hotel. This is my second Graduate hotel that I’m staying in and they are very efficient.

Reviewed on Mar 16, 2026

The Royal Sonesta Harbor Court Baltimore

The Royal Sonesta Harbor Court Baltimore

4.5 out of 5
Otterbein
Price was $779, price is now $601 per person
$601
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,800 reviews)
Great hotel, and a very good location convenient to a lot of great restaurants sent to the convention center. The only issue I had was that the restaurant and bar were minimally staffed. I’d hoped to find a lot more lively a hospitality aspect at the hotel. But the rooms were nice and quiet.

Reviewed on Mar 19, 2026

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
Price was $895, price is now $696 per person
$696
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,019 reviews)
Size of the room was nice we stayed in a king suite we had room to get dressed and not crash into each other. We also went to the gym it was small but four people were able to work out at the same time if two are on the machines for cardio. The store was great and check in was easy the parking on the side was helpful. Comfy bed. We didn’t have a smart tv so no Netflix but some good movies were on.

Reviewed on Mar 18, 2026

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
Beautiful troll downtown Annapolis... #Adventure

Historic District

2 out of top 10 points of interest in this area
5/5(85 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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is $195 total per night from Mar 29 to Mar 30
$195 total
per night
Mar 29 - Mar 30
9.4/10 Exceptional! (1,004 reviews)
The hotel has cute and trendy decor. It’s located centrally nearby many restaurants and coffee shops around. Our room was clean and spacious. Check in was easy and on point. We had no issues with this hotel. This is my second Graduate hotel that I’m staying in and they are very efficient.

Reviewed on Mar 16, 2026

Graduate by Hilton Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is $125 total per night from Mar 24 to Mar 25
$125 total
per night
Mar 24 - Mar 25
8.8/10 Excellent! (1,001 reviews)
Great bar.

Reviewed on Mar 20, 2026

Crowne Plaza Annapolis 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
The price is $179 total per night from Apr 2 to Apr 3
$179 total
per night
Apr 2 - Apr 3
9/10 Wonderful! (1,868 reviews)
The elevator was not working the entire time.

Reviewed on Mar 13, 2026

Historic Inns of Annapolis
See all 1,196 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

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

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

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

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

$30
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
From haunted harbors to pirate hideouts, the ghosts of Annapolis await.

Ashes and Apparitions of Annapolis Ghost Tour

$32
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
Food Tour Plate

Historic Annapolis Food Tour

$80
per adult
Historic Annapolis Food 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.