Oyster Harbor Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by KaiG

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

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 NZ$163 per night from 4 Jan to 5 Jan
NZ$163
4 Jan - 5 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Great place!

Reviewed on 3 Dec 2025

DoubleTree by Hilton Hotel 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
8.8/10 Excellent! (1,915 reviews)
Upon entering the entire stay was a 10. The valet, seperate, were very courteous. The front desk staff were friendly and extremely helpful. The hotel was decorated for Christmas and was very festive. The room was clean and very roomy. The location could not have been better, directly across from ...

Reviewed on 3 Dec 2025

Get rates
Historic Inns of Annapolis
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 NZ$191 per night from 15 Dec to 16 Dec
NZ$191
15 Dec - 16 Dec
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Excellent from check in to check out, highly recommend!

Reviewed on 7 Dec 2025

Crowne Plaza Annapolis by IHG
See all 1,195 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.

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

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
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

Anne Arundel Medical Center

If Anne Arundel Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Parole.

Anne Arundel Medical Center

Activities

Costa Rica Rainforest Guided Tram Tour

AERIAL TRAM TOUR - HALF DAY PASS Rainforest Adventures Jacó

NZ$119
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

NZ$71
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Phantoms of Annapolis Ghost Tour By US Ghost Adventures

Ashes and Apparitions of Annapolis Ghost Tour

NZ$57
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
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.