Oyster Harbor Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by KaiG

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

1 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

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! (1,817 reviews)
"Liked the historic feel and the archeological dig site located just off the lobby (and still inside the hotel)! Tahina gave excellent customer support"

Reviewed on 8 Aug 2025

Get rates
Historic Inns of 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 4.085.232 ₫ per night from 17 Aug to 18 Aug
4.085.232 ₫
4.657.164 ₫ total
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"This hotel is great. Good location accommodations are beautiful. The only thing they lack is a coffee maker in the room."

Reviewed on 7 Aug 2025

Graduate by Hilton 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 2.540.815 ₫ per night from 17 Aug to 18 Aug
2.540.815 ₫
2.896.529 ₫ total
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"You all have some of the best staff ever. I liked the property so much that I’m planning my next trip to stay again already. My grandkids love the idea that we can just go downstairs to get breakfast and make your own waffles. Last but not least, the hot tub and swimming pool is on point."

Reviewed on 7 Aug 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,202 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 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

Annapolis City Dock

You can enjoy retail therapy at Annapolis City Dock during your trip to Annapolis. Stroll along the area's waterfront or simply savour its top-notch restaurants.

Annapolis City Dock