Oyster Harbor Vacation Packages

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Top Holiday Package Deals in Oyster Harbor

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
per person
Sep 3 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
8.2/10 Very Good! (1,005 reviews)
I really enjoyed my stay. Staff was excellent. It was quite and very comfortable

Reviewed on Jul. 27, 2025

Hilton Baltimore Inner Harbor

Hilton Baltimore Inner Harbor

4 out of 5
Downtown West
per person
Aug 27 - Sep 3
found 17 hours ago
Roundtrip flight included
Vancouver (YVR) to Baltimore (BWI)
8.4/10 Very Good! (1,004 reviews)
The only aggravating issue we had is that we could not find the Hilton parking ramp. The directions we were given by the doormen and clerks were not clear. We initially had to park blocks away. Having a map of where to enter the parking lot would have saved us a couple of hours of aggravation.

Reviewed on Jul. 27, 2025

The William Fell Baltimore, Tapestry Collection by Hilton

The William Fell Baltimore, Tapestry Collection by Hilton

3.5 out of 5
Fells Point
per person
Aug 27 - Sep 3
found 17 hours ago
Roundtrip flight included
Vancouver (YVR) to Baltimore (BWI)
9.2/10 Wonderful! (37 reviews)
Hotel was great. The front staff was not very helpful but everything else was great

Reviewed on Jul. 26, 2025

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
per person
Aug 27 - Sep 3
found 17 hours ago
Roundtrip flight included
Vancouver (YVR) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
Room was great for price. Lots of restaurants and close to Towson University.

Reviewed on Jul. 14, 2025

Hotel Revival Baltimore

Hotel Revival Baltimore

4 out of 5
Mount Vernon
per person
Sep 3 - Sep 10
found 15 hours ago
Roundtrip flight included
Vancouver (YVR) to Baltimore (BWI)
9.4/10 Exceptional! (1,011 reviews)
Clean rooms and easy check in

Reviewed on Jul. 19, 2025

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

Discover a well-preserved historic district with elements of the original town plan, featuring landmarks like the Maryland State House, St. Ann's Church, and Paca House and Gardens. The neighborhood features prestigious educational institutions like St. John's College and the U.S. Naval Academy.

Find hotels in Historic District

Oyster Harbor Hotel Deals

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
The price is CA $140 per night from Aug 3 to Aug 4
CA $140
CA $206 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,822 reviews)
"Great place for a quick get away!"

Reviewed on Jul. 26, 2025

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 CA $212 per night from Aug 3 to Aug 4
CA $212
CA $242 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (1,007 reviews)
"Very clean and comfortable. Shuttle stops right across the street. My only recommendation would be to put a keurig coffee maker in each room."

Reviewed on Jul. 25, 2025

Graduate by Hilton Annapolis
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 CA $134 per night from Aug 3 to Aug 4
CA $134
CA $153 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (1,015 reviews)
"Beautiful property, I just wasn’t a fan of the layout. It felt like I had to walk a mile from the lobby to the elevator to get to my room. Also, one of the days of my stay there was a wedding reception. The location of my room meant that I had to walk through the reception crowd to get to the elevators ..."

Reviewed on Jul. 25, 2025

DoubleTree by Hilton Hotel 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations

Frequently asked questions

How much does an Oyster Harbor vacation package cost?
Create unforgettable memories with our Oyster Harbor vacation packages, which start from only CA $678. 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 Harbor?
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 Harbor vacation 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 vacation in Oyster Harbor is much closer than you thought!
Where should I stay in Oyster Harbor?
Most people who travel to Oyster Harbor 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 Harbor?
Reserve a room at Waterfront Chesapeake Cottage In Oyster Bay. It's one of this neighborhood's most in-demand properties. Another top-rated option in Oyster Harbor is Cozy Cottage By The Beach - Waterviewminutes From Downtown Annapolis.
How far in advance should I book my Oyster Harbor vacation?
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 Harbor sometimes occur a few weeks before the date of departure.
What does an Expedia Oyster Harbor travel package include?
With Expedia, you can select a combination of hotels, flights and car rentals to create your ideal Oyster Harbor 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 Harbor 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 vacation is only a few clicks away.
Can I choose my airline with an Oyster Harbor Expedia vacation 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 Harbor vacation package?
Don't worry if you're rethinking your Oyster Harbor vacation 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 military items, interior views and heritage architecture

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
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

Things to do

Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

CA $36
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

CA $55
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Half Day Private Tour of Annapolis Up to 12 people

Half Day Private Bus Tour of Annapolis Up to 13 people

CA $2,238
per traveller
Half Day Private Bus Tour of Annapolis Up to 13 people
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.