Oyster Harbor Vacations from ￥56,084

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 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

The Latest Oyster Harbor Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was ￥69,406, price is now ￥56,084 per person
￥56,084
per person
Sep 29 - Oct 1
found 1 hour ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
8.4/10 Very Good! (2,841 reviews)
I

Reviewed on Jul 18, 2026

Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Price was ￥141,136, price is now ￥117,383 per person
￥117,383
per person
Sep 29 - Oct 1
found 1 hour ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
9.4/10 Exceptional! (1,005 reviews)
Great hotel. Great location. Very clean. Exceptionally helpful staff. An all around great experience.

Reviewed on Jul 18, 2026

ROOST White House

ROOST White House

2.5 out of 5
Downtown Washington D.C.
Price was ￥382,055, price is now ￥323,142 per person
￥323,142
per person
Aug 24 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Baltimore (BWI)
9.4/10 Exceptional! (69 reviews)
Really nice apartment hotel, high end, large space, great location, and helpful staff.

Reviewed on Jul 18, 2026

Hotel Washington

Hotel Washington

5 out of 5
Downtown Washington D.C.
Price was ￥370,757, price is now ￥315,312 per person
￥315,312
per person
Aug 24 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Baltimore (BWI)
9/10 Wonderful! (2,426 reviews)
Well located. Clean. Nice and cool when hot outside. Didn’t use the restaurant and bar areas. Good place to get back to after a long day exploring.

Reviewed on Jul 18, 2026

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Price was ￥379,458, price is now ￥326,698 per person
￥326,698
per person
Aug 24 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Baltimore (BWI)
9.4/10 Exceptional! (1,214 reviews)

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
An aerial view of a coastal town with a prominent church, dense residential area, and a marina with boats.

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 ￥18,511 per night from Aug 2 to Aug 3
￥18,511
￥26,657 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (1,884 reviews)
"Nice staff"

Reviewed on Jul 18, 2026

Historic Inns of 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 ￥18,510 per night from Aug 2 to Aug 3
￥18,510
￥21,101 total
Aug 2 - Aug 3
includes taxes & fees
8.8/10 Excellent! (1,031 reviews)
"Nice, comfortable room, friendly staff gave us cookies and bottled water at check in."

Reviewed on Jul 19, 2026

DoubleTree by Hilton Hotel 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 ￥19,163 per night from Aug 2 to Aug 3
￥19,163
￥21,846 total
Aug 2 - Aug 3
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Great"

Reviewed on Jul 18, 2026

Crowne Plaza Annapolis by IHG
See all 1,203 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 ￥56,084. 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.

Things to do

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

￥4,876
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Kent Narrows Sunset Cruise

Kent Narrows Sunset Cruise

￥6,493
per adult
Kent Narrows Sunset Cruise
Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

￥5,201
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.