Oyster Harbor Holidays

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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.

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

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$202 per night from 1 Jul to 2 Jul
AU$202
per night
1 Jul - 2 Jul
8.6/10 Excellent! (1,001 reviews)
Salvaged stay after other hotel experience
"After having to leave my first reservation (different hotel). This was paradise. Courteous, helpful staff. Comfortable room and beds."

Reviewed on 27 May 2024

DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
The price is AU$235 per night from 1 Jul to 2 Jul
AU$235
per night
1 Jul - 2 Jul
8.8/10 Excellent! (1,623 reviews)
"We had a pleasant stay at the Maryland Inn. It was a beautiful room and nicely appointed. The staff service was very good.My only disappointment was the towels were in need of upgrade ( old and worn), pillows were too firm (foam). Otherwise it was a very experience."

Reviewed on 2 Jun. 2024

Historic Inns of Annapolis
Crowne Plaza Annapolis, an IHG Hotel
Crowne Plaza Annapolis, an IHG Hotel
3.5 out of 5
173 Jennifer Rd, Annapolis, MD
The price is AU$215 per night from 6 Jun to 7 Jun
AU$215
per night
6 Jun - 7 Jun
8.6/10 Excellent! (1,004 reviews)
"Liked free parking and convinient &near to shopping"

Reviewed on 30 May 2024

Crowne Plaza Annapolis, an IHG Hotel
See all 1,121 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

More holiday ideas

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