Oyster Harbor Holidays from AU$560

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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.

Top Holiday Package Deals in Oyster Harbor

Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Laurel near Fort Meade

Sleep Inn & Suites Laurel near Fort Meade

2.5 out of 5
North Laurel
Price was AU$615, price is now AU$560 per person
AU$560
per person
27 Oct - 31 Oct
found 1 hour ago
Return direct flight included
Toronto (YYZ) to Baltimore (BWI)
6.8/10 (1,006 reviews)
Great place for rest

Reviewed on 26 Aug 2025

Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Price was AU$762, price is now AU$656 per person
AU$656
per person
27 Oct - 31 Oct
found 1 hour ago
Return direct flight included
Toronto (YYZ) to Baltimore (BWI)
8.6/10 Excellent! (1,007 reviews)
Dennis was a great bartender! Such a nice guy and the service was great!! 😊

Reviewed on 23 Sept 2025

Comfort Inn Laurel - Fort Meade

Comfort Inn Laurel - Fort Meade

2.5 out of 5
Price was AU$670, price is now AU$605 per person
AU$605
per person
27 Oct - 31 Oct
found 1 hour ago
Return direct flight included
Toronto (YYZ) to Baltimore (BWI)
8/10 Very Good! (1,010 reviews)
Not one of the better properties I have stayed at.

Reviewed on 23 Sept 2025

Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

3 out of 5
Price was AU$649, price is now AU$588 per person
AU$588
per person
27 Oct - 31 Oct
found 1 hour ago
Return direct flight included
Toronto (YYZ) to Baltimore (BWI)
7.8/10 Good! (210 reviews)
Staff was great , easy in and out

Reviewed on 24 Sept 2025

La Quinta Inn & Suites by Wyndham Columbia / Fort Meade

La Quinta Inn & Suites by Wyndham Columbia / Fort Meade

3 out of 5
Price was AU$714, price is now AU$655 per person
AU$655
per person
27 Oct - 31 Oct
found 1 hour ago
Return direct flight included
Toronto (YYZ) to Baltimore (BWI)
7.8/10 Good! (1,007 reviews)
For a quick stop, it was perfect for me, clean and quiet.

Reviewed on 28 Aug 2025

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 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(2 area reviews)

While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.

Find hotels in Historic District

Our pick of the best 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! (1,853 reviews)
"Good"

Reviewed on 25 Sept 2025

Get rates
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 AU$183 per night from 29 Sept to 30 Sept
AU$183
29 Sept - 30 Sept
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 21 Sept 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 AU$175 per night from 6 Oct to 7 Oct
AU$175
6 Oct - 7 Oct
includes taxes & fees
9/10 Wonderful! (1,022 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 22 Sept 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
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Cheap Holidays
beach holidays
Beach Holidays
Beach 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 AU$560. 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

U.S. Naval Academy featuring heritage architecture, interior views and military items

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
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

Activities

Food Tour Plate

Historic Annapolis Food Tour

AU$121
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

AU$48
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Raise a toast to spirits of both kinds on our Haunted Bar Crawl!

Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

AU$54
per adult
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
See all activities in Annapolis
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.