Oyster Harbor Vacation Packages 2026 from $261

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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.

The Quincy, an Ascend Collection Hotel

Downtown Washington D.C.

Save 100% on your flight

$261

per person

Dec 2 - Dec 5

found 17 hours ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.2/10 Wonderful! (1,137 reviews)

A great size room which was clean and comfortable. Great location for sightseeing and a good variety of restaurants within walking distance. Staff were friendly and helpful.

Reviewed on Oct 15, 2026

The Darcy Hotel

Downtown Washington D.C.

Save 100% on your flight

$343

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.2/10 Wonderful! (1,716 reviews)

Swanendele Inn at St. Mary's Maryland

Save 100% on your flight

$1,196

per person

Nov 17 - Nov 21

found 24 hours ago

Roundtrip flight included

Los Angeles (LAX) to Baltimore (BWI)

9.8/10 Exceptional! (35 reviews)

Fantastic location. Great breakfast. Very gracious hosts.

Reviewed on Oct 13, 2026

Nice House

Groveton

Save 100% on your flight

$1,171

per person

Jan 2 - Jan 5

found 23 hours ago

Roundtrip flight included

Dallas (DFW) to Baltimore (BWI)

No reviews

Kimpton Hotel Monaco Washington DC by IHG

Downtown Washington D.C.

$483

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip flight included

Miami (MIA) to Baltimore (BWI)

8.4/10 Very Good! (1,003 reviews)

Nice place.

Reviewed on Oct 16, 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

An aerial view of a coastal town with a prominent church, dense residential area, and a marina with boats.

Historic District

2 out of top 10 points of interest in this area

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.

A marina with numerous sailboats docked, surrounded by residential houses and a backdrop of trees and a distant shoreline.

Eastport

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

A cityscape with historic buildings, a river, and a bridge in the background.

Murray Hill

While visiting Murray Hill, you might make a stop by sights like Spa Creek and Ballet Theater of Maryland.

A grassy area with two Adirondack chairs near a waterfront, a large tree, and a distant view of the sea.

Hillsmere

If you're spending some time in Hillsmere, Maryland Quiet Waters Park and Great Frogs Winery are top sights worth seeing.

A suspension bridge over a body of water with a sunset in the background.

Cape Saint Claire

Boasting three marinas, multiple parks and beaches, Cape St. Claire offers a shopping center and various churches, with easy access to Annapolis and the Chesapeake Bay Bridge via U.S. Route 50.

Oyster Harbor Hotel Deals

Graduate by Hilton Annapolis

126 West St Annapolis MD

Fully refundableReserve now, pay when you stay

$147 nightly

$167 total

Oct 26 - Oct 27

Total with taxes and fees

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

Fully refundableReserve now, pay when you stay

$111 nightly

$126 total

Oct 19 - Oct 20

Total with taxes and fees

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD

Fully refundableReserve now, pay when you stay

$132 nightly

$146 total

Oct 27 - Oct 28

Total with taxes and fees

8.6/10 Excellent! (1,003 reviews)

"Great rooom, really great service."

Reviewed on Oct 15, 2026

See all 1,235 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.