Oyster Harbor Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by KaiG
    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to AU$460 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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
Annapolis featuring a city and street scenes as well as a small group of people

Historic District

2 out of top 10 points of interest in this area
5/5(2 area reviews)

While visiting Historic District, you might make a stop by sights like Thurgood Marshall Memorial and Maryland State House.

Find hotel + flight trips in Historic District

Our pick of the best Oyster Harbor Hotel Deals

Crowne Plaza Annapolis, an IHG Hotel
Crowne Plaza Annapolis, an IHG Hotel
3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is AU$232 per night from 19 May to 20 May
AU$232
per night
19 May - 20 May
8.6/10 Excellent! (1,002 reviews)
"Parking limited on weekend evenings"

Reviewed on 28 Apr. 2024

Crowne Plaza Annapolis, an IHG Hotel
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 AU$293 per night from 28 May to 29 May
AU$293
per night
28 May - 29 May
8.8/10 Excellent! (1,612 reviews)
"The location was excellent, the room wss very nice bit was decorated in a fashion that was too modern give the name of the hotel. The staff was friendly and efficient but said they would send an Anniversary present to our room but it never arrived. The facility was good but the elevator was too ..."

Reviewed on 9 May 2024

Historic Inns of Annapolis
Graduate Annapolis
Graduate Annapolis
4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$348 per night from 12 Jun to 13 Jun
AU$348
per night
12 Jun - 13 Jun
9.2/10 Wonderful! (1,052 reviews)
"Unique property, close to everything. Costly, but every hotel in the area is."

Reviewed on 12 May 2024

Graduate Annapolis
See all 1,147 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
beach holidays

Beach Holidays

Beach Holidays
family friendly holidays

Family Friendly Holidays

Family Friendly Holidays

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.

Discover the most popular places to visit in Oyster Harbor

Image for U.S. Naval Academy

U.S. Naval Academy

4/5(3 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
Image for Sandy Point State Park

Sandy Point State Park

Sunbathe on the beach, enjoy unrivaled views of the Chesapeake Bay Bridge and go hiking, swimming, fishing and boating in this vast park.

Sandy Point State Park
Image for Chesapeake Bay Bridge

Chesapeake Bay Bridge

5/5(1 review)

Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.

Chesapeake Bay Bridge

Activities

Image for Historic Annapolis Food Tour

Historic Annapolis Food Tour

AU$115
Per adult
Historic Annapolis Food Tour
Image for Half Day Private Bus Tour of Annapolis Up to 13 people

Half Day Private Bus Tour of Annapolis Up to 13 people

AU$2,568
Per adult
Half Day Private Bus Tour of Annapolis Up to 13 people
Image for Phantoms of Annapolis Ghost Tour By US Ghost Adventures

Phantoms of Annapolis Ghost Tour By US Ghost Adventures

AU$45
Per adult
Phantoms of Annapolis Ghost Tour By US Ghost Adventures
See all activities in Annapolis

More holiday ideas

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