Oyster Harbor Holidays

Photo by KaiG

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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 showing 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

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

Find hotels in Historic District

Top hotels in Oyster Harbor

Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

Annapolis MD
8.8/10 Excellent! (11 reviews)
Lovely house, had everything we needed for a quick business trip.

Reviewed on 12 Oct 2025

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Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
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 €73 per night from 8 Feb to 9 Feb
€73
8 Feb - 9 Feb
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Clean and we moved to a quiet room as well

Reviewed on 8 Jan 2026

DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is €144 per night from 25 Jan to 26 Jan
€144
25 Jan - 26 Jan
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
Pleasant staff. Good location to walk to restaurants, shops.

Reviewed on 30 Dec 2025

Graduate by Hilton Annapolis
See all 1,206 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.

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.

Popular places to visit

Chesapeake Bay Bridge

Chesapeake Bay Bridge

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

Chesapeake Bay Bridge
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
Maryland State House showing an administrative building and heritage architecture

Maryland State House

Appreciate the superb architecture and fascinating history of America’s first peacetime capitol and the oldest state capitol still in legislative use.

Maryland State House

Things to do

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

€34
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

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

€8
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Let’s Roam Scavenger Hunt, Annapolis, Maryland

Self-Guided Scavenger Hunt: Annapolis Red Bricks & Blue Views

€13
per adult
Self-Guided Scavenger Hunt: Annapolis Red Bricks & Blue Views
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.