Oyster Harbor Vacations

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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

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

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
8.8/10 Excellent! (1,790 reviews)
"Perfect for those that love American history"

Reviewed on Jun 29, 2025

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Historic Inns of 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
The price is ₩136,543 per night from Jul 21 to Jul 22
₩136,543
₩155,659 total
Jul 21 - Jul 22
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"The warm cookie at check-in from Tyler was a thoughtful and welcoming gesture. I appreciated the friendly front desk team, the clean and comfortable room, and the hotel’s convenient location. The overall ambiance was inviting and well cared for."

Reviewed on Jun 29, 2025

DoubleTree by Hilton Hotel Annapolis
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ₩138,531 per night from Jul 21 to Jul 22
₩138,531
₩157,925 total
Jul 21 - Jul 22
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"Parking situation was awful and needs to be rethought. The extra cost for parking was ridiculous and spaces not sufficient for hotel capacity."

Reviewed on Jun 27, 2025

Hilton Garden Inn Annapolis Downtown
See all 1,205 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.

Frequently asked questions

How much does an Oyster Harbor vacation package cost?
Create unforgettable memories with our Oyster Harbor vacation packages, which start from only . Pick the flights and hotels that match your travel style. Then, add on one or two tours or experiences for an incredible escape.
How do I get a cheap travel package to Oyster Harbor?
Bundle your bookings with Expedia to save big on your next getaway. With over 550 air carriers and 1,000,000 properties across the globe, your Oyster Harbor vacation package can be tailored exactly to suit your budget. With all those extra dollars, why not include a few interesting tours and activities? It's an easy way to unlock even more bargains. Your dream vacation in Oyster Harbor is much closer than you thought!
Where should I stay in Oyster Harbor?
Most people who travel to Oyster Harbor include both U.S. Naval Academy and Maryland State House on their must-see lists. Why not go for a hotel close to one of these fantastic attractions?
What are the top hotels in Oyster Harbor?
Reserve a room at Waterfront Chesapeake Cottage In Oyster Bay. It's one of this neighborhood's most in-demand properties. Another top-rated option in Oyster Harbor is Cozy Cottage By The Beach - Waterviewminutes From Downtown Annapolis.
How far in advance should I book my Oyster Harbor vacation?
Browse Expedia to compare international airfares as soon as possible. You can usually purchase a ticket up to 12 months before departure. If it's too early for your preferred air carrier, or you've left things to the last minute, fear not. Cheap tickets to Oyster Harbor sometimes occur a few weeks before the date of departure.
What does an Expedia Oyster Harbor travel package include?
With Expedia, you can select a combination of hotels, flights and car rentals to create your ideal Oyster Harbor travel package. Once you've made your booking, you can add on all the fun stuff like activities and tours. Remember, the more you bundle, the more deals you'll score!
What should I know before booking an Oyster Harbor travel package?
Discover deals to suit your budget with an Expedia package. Flights, hotels, rental cars --- we've got them all. You'll save a tidy sum just by bundling your bookings. Whether you're going on a winter adventure or kicking back on a warm beach, your dream vacation is only a few clicks away.
Can I choose my airline with an Oyster Harbor Expedia vacation package?
Yes, and with over 550 airlines to pick from all over the world, you have plenty of choice. Look through the available options and find out which airline best fits your budget and needs.
If I'm not able to travel, can I cancel my Oyster Harbor vacation package?
Don't worry if you're rethinking your Oyster Harbor vacation package --- it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We totally get that life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we're ready to help.

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
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.