Oyster Harbor Holidays from AU$10,560

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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.
Canopy by Hilton Washington DC The Wharf

Canopy by Hilton Washington DC The Wharf

4 out of 5
The Wharf
Price was AU$10,716, price is now AU$10,560 per person
AU$10,560
per person
16 Jan - 18 Jan
found 8 hours ago
Return direct flight included
Tunis (TUN) to Baltimore (BWI)
17.6/10 Exceptional! (1,004 reviews)
The room was awesome! The only negative thing i could say is the lobby is not properly identified, so you don't know where to check in, and the elevator controls are messed up at best. We couldn't figure out how to use them. Never been in an elevator without floor buttons before! But the hotel itself is beautiful, with beautiful rooms, and valet parking inside. We had a wonderful stay, and will definitely be staying there again in the future.

Reviewed on 24 Nov 2025

The Elegant Spring House Loft

The Elegant Spring House Loft

2 out of 5
Northwest
Price was AU$12,390, price is now AU$12,138 per person
AU$12,138
per person
16 Jan - 18 Jan
found 8 hours ago
Return direct flight included
Tunis (TUN) to Baltimore (BWI)
No reviews
The Serene Spring House Retreat

The Serene Spring House Retreat

2 out of 5
Northwest
Price was AU$12,210, price is now AU$11,981 per person
AU$11,981
per person
16 Jan - 18 Jan
found 8 hours ago
Return direct flight included
Tunis (TUN) to Baltimore (BWI)
No reviews
Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Price was AU$10,814, price is now AU$10,667 per person
AU$10,667
per person
16 Jan - 18 Jan
found 8 hours ago
Return direct flight included
Tunis (TUN) to Baltimore (BWI)
18/10 Exceptional! (1,002 reviews)
It was a great stay. Friendly and amenable staff and everything was very clean.

Reviewed on 24 Nov 2025

Hilton Washington DC National Mall The Wharf

Hilton Washington DC National Mall The Wharf

4 out of 5
Southwest
Price was AU$10,674, price is now AU$10,567 per person
AU$10,567
per person
16 Jan - 18 Jan
found 8 hours ago
Return direct flight included
Tunis (TUN) to Baltimore (BWI)
18/10 Exceptional! (1,236 reviews)
Clean room and staff was courteous

Reviewed on 23 Nov 2025

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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

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 hotels in Historic District

Our pick of the best Oyster Harbor Hotel Deals

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is AU$182 per night from 30 Nov to 1 Dec
AU$182
30 Nov - 1 Dec
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
No hot shower in Suite for three days

Reviewed on 19 Nov 2025

Crowne Plaza Annapolis by IHG
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! (1,900 reviews)
Good location

Reviewed on 20 Nov 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$106 per night from 21 Dec to 22 Dec
AU$106
21 Dec - 22 Dec
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
Everything was great

Reviewed on 19 Nov 2025

DoubleTree by Hilton Hotel Annapolis
See all 1,194 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.
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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$10,560. 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

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
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

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

AU$15
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Costa Rica Rainforest Guided Tram Tour

AERIAL TRAM TOUR - HALF DAY PASS Rainforest Adventures Jacó

AU$102
per adult
AERIAL TRAM TOUR - HALF DAY PASS Rainforest Adventures Jacó
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

AU$62
per adult
Annapolis Ghosts: Spirits & Spirits 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.