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
The price is ₩157,958 per night from Oct 27 to Oct 28
₩157,958
₩228,283 total
Oct 27 - Oct 28
includes taxes & fees
8.8/10 Excellent! (1,856 reviews)
"This was such a great place. I really enjoyed it and how great it was. The location was great. And the staff was great. I liked the nice people."

Reviewed on Sep 27, 2025

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 ₩149,119 per night from Sep 30 to Oct 1
₩149,119
₩169,995 total
Sep 30 - Oct 1
includes taxes & fees
8.6/10 Excellent! (1,015 reviews)
McMullen Symposium
"Clean room, efficient staff and superb breakfast. Grateful thanks to the hotel staff."

Reviewed on Sep 21, 2025

DoubleTree by Hilton Hotel Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
The price is ₩142,592 per night from Oct 14 to Oct 15
₩142,592
₩162,555 total
Oct 14 - Oct 15
includes taxes & fees
9/10 Wonderful! (1,023 reviews)
"This was a convenient property for visiting the Naval Academy and historic Annapolis. The property seemed to be well taken care of. The breakfast was the usual breakfast area with a waffle maker, oatmeal, a hot serving dish of an egg product, a meat, and a potato product. Nothing fancy. The room ..."

Reviewed on Sep 22, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,232 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

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
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.