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.
Hilton Garden Inn BWI Airport

Hilton Garden Inn BWI Airport

3 out of 5
per person
Apr. 15 - Apr. 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.4/10 Very Good! (1,005 reviews)
False Fire alarm interrupted sleep.

Reviewed on Mar. 1, 2025

DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
per person
Apr. 17 - Apr. 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
8.2/10 Very Good! (1,415 reviews)
Great staff, accommodated me very well since I am Deaf.

Reviewed on Feb. 28, 2025

Ulysses, an Ash Hotel

Ulysses, an Ash Hotel

4 out of 5
Mount Vernon
per person
Apr. 4 - Apr. 11
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
9.2/10 Wonderful! (663 reviews)
This is a unique hotel, the vibe is great! The bars were cool, the staff was great! The rooms are not a traditional but I was comfortable enough. I would recommend

Reviewed on Feb. 25, 2025

The Westin Baltimore Washington Airport - BWI

The Westin Baltimore Washington Airport - BWI

4 out of 5
per person
May 17 - May 19
just found
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.6/10 Excellent! (1,015 reviews)
Everything was GREAT, EXCEPT for the fire alarm going off

Reviewed on Mar. 1, 2025

Metro Points Hotel

Metro Points Hotel

3 out of 5
per person
May 21 - May 23
found 19 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
7.2/10 Good! (1,190 reviews)
Everything was nice but the ice machine wasn’t working.

Reviewed on Feb. 25, 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 which includes 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

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 $244 per night from Mar. 7 to Mar. 8
CA $244
CA $326 total
includes taxes & fees
Mar 7 - Mar 8
8.8/10 Excellent! (1,673 reviews)
"Superb location. Very nice rooms with ample space and great decor. Friendly and responsive staff. There were a couple items that kept it from 5 star. The hotel hosts many outside events in their ballroom during the day and the only access is through the main lobby. Attendees walk through the small ..."

Reviewed on Feb. 26, 2025

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
Fully refundable
The price is CA $129 per night from Mar. 9 to Mar. 10
CA $129
CA $147 total
includes taxes & fees
Mar 9 - Mar 10
8.6/10 Excellent! (1,001 reviews)
"N/a"

Reviewed on Feb. 22, 2025

Crowne Plaza Annapolis, an IHG Hotel
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 Mar. 18 to Mar. 19
CA $134
CA $153 total
includes taxes & fees
Mar 18 - Mar 19
8.4/10 Very Good! (1,000 reviews)
Nice Hotel Great Lication
"Comfortable and clean hotel. Staff was very friendly and receptive. TV was great and shower which included body wash, shampoo, and conditioner was nice. My only issue is that Hotels.com advertised 50$ pet fee which wasn’t honored. Charged 75$."

Reviewed on Feb. 24, 2025

DoubleTree by Hilton Hotel Annapolis
See all 1,146 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

Beach Vacations

Family Vacations

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 $498. 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

4.5/5(8 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
Chesapeake Bay Bridge

Chesapeake Bay Bridge

4.5/5(2 reviews)

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

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
Food Tour Plate

Historic Annapolis Food Tour

CA $113
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Annapolis Ghost Tour: Phantoms of Annapolis

CA $48
per adult
Annapolis Ghost Tour: Phantoms of Annapolis
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.