Oyster Harbor Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
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Your Oyster Harbour Holiday
Make planning your travels hassle-free by booking a holiday package to Oyster Harbour. We'll take care of the finer points, so you can concentrate on discovering everything this neighbourhood can offer. Not sure what to see and do during your trip to Oyster Harbour? 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 holiday to Oyster Harbour, Expedia will help you get there.
Our guide on 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
Historic District
2 out of top 10 points of interest in this area
While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.
Eastport
While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.
Murray Hill
If you're spending some time in Murray Hill, Spa Creek and Ballet Theater of Maryland are top sights worth seeing.
Hillsmere
While visiting Hillsmere, you might make a stop by sights like Maryland Quiet Waters Park and Great Frogs Winery.
Admiral Heights
If you're looking for some top things to see and do in Admiral Heights and surrounding area, you can visit Navy-Marine Corps Memorial Stadium and Maryland Hall for Creative Arts.
Our pick of the best Oyster Harbor Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
AU$133
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (1,179 reviews)
"From the check in to the check out this was a great experience. The staff were super friendly and helpful, the room was clean and comfortable and the location was fantastic. Free and ample parking added to the pluses. This hotel is an Annapolis gem and we will definitely be staying there again."
Reviewed on 16 Sept 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
AU$209
12 Oct - 13 Oct
includes taxes & fees
9/10 Wonderful! (1,997 reviews)
"Very impressed with the staff and all the help they provided for us.....! Cleanliness tops. My only complaint is with the cable TV quality. Very poor picture quality and cumbersome remote. This certainly requires a big upgrade. Also it wasn`t till the second day that I found electric outlets for ..."
Reviewed on 16 Sept 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
AU$176
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (1,016 reviews)
"Clerk was very informational, great room, Breakfast was only $18 each and filled us up! Great service and plenty of parking. Very much worth the value."
Reviewed on 17 Sept 2026
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 Harbour holiday package cost?
Create unforgettable memories with our Oyster Harbour holiday 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 Harbour?
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 Harbour holiday 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 holiday in Oyster Harbour is much closer than you thought!
Where should I stay in Oyster Harbour?
Most people who travel to Oyster Harbour 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 Harbour?
Reserve a room at Waterfront Chesapeake Cottage In Oyster Bay. It's one of this neighbourhood's most in-demand properties. Another top-rated option in Oyster Harbour is Cosy Cottage By The Beach - Waterviewminutes From Downtown Annapolis.
How far in advance should I book my Oyster Harbour holiday?
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 Harbour sometimes occur a few weeks before the date of departure.
What does an Expedia Oyster Harbour travel package include?
With Expedia, you can select a combination of hotels, flights and car rentals to create your ideal Oyster Harbour 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 Harbour 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 holiday is only a few clicks away.
Can I choose my airline with an Oyster Harbour Expedia holiday 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 Harbour holiday package?
Don't worry if you're rethinking your Oyster Harbour holiday 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.
Activities
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
AU$14
per traveller
80% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
AU$36
per adult
100% of travellers recommend
Best of Annapolis Tour: Colonial, State House, Naval Academy
AU$47
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.