Oyster Harbor Holidays

Book a Hotel + Flight or Car together to unlock savings

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
Beautiful troll downtown Annapolis... #Adventure

Historic District

2 out of top 10 points of interest in this area

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

Find hotels in Historic District

Top hotels in Oyster Harbor

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
Fully refundableReserve now, pay when you stay
The price is 2.363.179 ₫ per night from 22 Mar to 23 Mar
2.363.179 ₫
2.694.025 ₫ total
22 Mar - 23 Mar
includes taxes & fees
8.8/10 Excellent! (991 reviews)
Room was clean. All of the staff that I interacted with was so great!

Reviewed on 19 Feb 2026

Sonesta ES Suites 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 4.237.621 ₫ per night from 22 Mar to 23 Mar
4.237.621 ₫
4.830.888 ₫ total
22 Mar - 23 Mar
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
Courteous, professional staff. Clean room. Good parking. Great location within walking distance of restaurants, stores, and the State House. I would stay here again when are in Annapolis, Maryland.

Reviewed on 15 Feb 2026

Graduate by Hilton Annapolis
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
9/10 Wonderful! (1,886 reviews)
This is a beautiful old historic hotel in the heart of Annapolis. It is the perfect central location if doing work with the MD General Assembly - adjacent to the Statehouse and just a block from legislator offices. You are also within a couple blocks of Main Street which full of small bars, restaurants, ...

Reviewed on 18 Feb 2026

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Historic Inns of Annapolis
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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 1null000null000 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

Sandy Point State Park

Sandy Point State Park

Enjoy a trip to Sandy Point State Park and popular activities such as boating in Annapolis. Stroll along the area's waterfront or simply savour its top-notch restaurants.

Sandy Point State Park
Maryland State House showing heritage architecture and an administrative building

Maryland State House

After visiting Maryland State House, make a plan to see the other sights and activities in Annapolis. While you're in the area, stroll along the waterfront.

Maryland State House
Hammond-Harwood House

Hammond-Harwood House

You can browse the exhibits at Hammond-Harwood House, a museum with a story of its own, during your travels to Annapolis. Wander the area's waterfront or simply enjoy one of its top-notch restaurants.

Hammond-Harwood House