Oyster Harbor Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Cape Saint Claire
While visiting Cape Saint Claire, you might make a stop by sights like Northern Chesapeake Bay and Chesapeake Bay.
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
NZ$189
30 Aug - 31 Aug
includes taxes & fees
8.8/10 Excellent! (1,093 reviews)
"Room was clean. Staff were friendly. The area shuttle was a wonderful amenity to have access to with friendly drivers! The no my opportunity to note is the air conditioning was inconsistent getting very cold then cycling off to very warm making it hard to sleep comfortably during a summer stay."
Reviewed on 11 Aug 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
NZ$236
25 Aug - 26 Aug
includes taxes & fees
9/10 Wonderful! (1,945 reviews)
"Our stay was overall good. The room stayed cool during a very hot weekend. It is so conveniently located! Our only opportunity to note is that our housekeeping was inconsistent. Day 2 we were in the room and we asked if the house keeper could come back. They never came back. Day 3 the house keeper ..."
Reviewed on 11 Aug 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
NZ$213
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,020 reviews)
"We had a great time at this hotel. Room was clean and cozy we spent time in the pool which did look bigger in the pictures but we still had fun. I would definitely stay again."
Reviewed on 10 Aug 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 Ghosts: Spirits & Spirits Haunted Pub Crawl
NZ$52
per adult
Annapolis Harbor and U.S. Naval Academy Cruise
NZ$59
per adult
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
NZ$17
per traveller
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.