Oyster Harbor Vacations from ￥126,588

Book a Hotel + Flight or Car together to unlock savings

Photo by KaiG

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

The Latest Oyster Harbor Vacation Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
Price was ￥145,933, price is now ￥126,588 per person
￥126,588
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
7.8/10 Good! (1,004 reviews)
The Largo Doubletree Hotel by Hilton was a pleasant venue. There was a mix-up with my reservation that was made resolute by the Manager on duty, Ms. Nordia. The entire hotel staff was courteous, kind, professional and helpful. The room colors and accommodations were tasteful. The dining room options for breakfast and lunch/dinner were great choices and enjoyable. The short summer getaway at this location was a good experience.

Reviewed on Aug 14, 2025

Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

4.5 out of 5
Downtown Baltimore
Price was ￥142,372, price is now ￥130,926 per person
￥130,926
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
9/10 Wonderful! (102 reviews)
This hotel is amazing. Very friendly, in a great location, and had no problems. My dog came with me and they did not give me a hard time or make me feel judged like other hotels have. Great walking distance, had complimentary wine hour and tea/coffee. 10/10 stay all around. We will be returning upon ventures in Bmore area!

Reviewed on Aug 18, 2025

Residence Inn by Marriott - Silver Spring

Residence Inn by Marriott - Silver Spring

3 out of 5
Price was ￥152,335, price is now ￥147,216 per person
￥147,216
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
9/10 Wonderful! (545 reviews)
This hotel was nice, clean and the staff was friendly. The breakfast in the morning was great and always well stocked. I would’ve given them 5 stars but I don’t agree with having to pay to park on the private hotel lot. I also don’t like the size of the bed, it’s listed as a queen but seemed more like a full size. Very small!

Reviewed on Aug 17, 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

1 out of top 10 points of interest in this area
5/5(83 area reviews)

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
8.8/10 Excellent! (1,836 reviews)
"There were no ghosts!"

Reviewed on Aug 20, 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 ￥23,606 per night from Sep 2 to Sep 3
￥23,606
￥26,911 total
Sep 2 - Sep 3
includes taxes & fees
9.2/10 Wonderful! (1,012 reviews)
"Very good"

Reviewed on Aug 20, 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 ￥14,863 per night from Sep 2 to Sep 3
￥14,863
￥16,943 total
Sep 2 - Sep 3
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"Decent place and price"

Reviewed on Aug 22, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,215 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 Harbor vacation package cost?
Create unforgettable memories with our Oyster Harbor vacation packages, which start from only ￥126,588. 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 which includes military items, interior views and heritage architecture

U.S. Naval Academy

4.5/5(446 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(270 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

4.5/5(13 reviews)

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

Food Tour Plate

Historic Annapolis Food Tour

￥11,824
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

￥3,843
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

￥4,434
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
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.