Oyster Harbor Vacations

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    Save up to ￥109,000 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
  • Terrace/patio
    Jul 6 - Jul 12

    Kellogg Conference Hotel at Gallaudet University + Flight

    Northeast
    6 nights
    3.0 star property
    8.2/10 - Very Good (1,001 reviews)
    "Parking detached from the actual hotel. Location setting is excellent and close to many shops and local"
    Reviewed May 12, 2026
    Roundtrip • Tokyo (HND) - Washington (IAD)
    HND - IAD • 1 stop DCA - NRT • 1 stop
    ￥1,195,417
    ￥553,112
    per traveler
    found 9 hours ago
    Kellogg Conference Hotel at Gallaudet University
  • Terrace/patio
    Jul 6 - Jul 12

    Kimpton Banneker Hotel by IHG + Flight

    Downtown Washington D.C.
    6 nights
    4.5 star property
    9.0/10 - Wonderful (817 reviews)
    "Absolutely superior hotel. Front desk staff amazing, clean well appointed rooms. "
    Reviewed May 19, 2026
    Roundtrip • Tokyo (HND) - Washington (IAD)
    HND - IAD • 1 stop DCA - NRT • 1 stop
    ￥1,213,224
    ￥566,040
    per traveler
    found 9 hours ago
    Kimpton Banneker Hotel by IHG
  • Lobby
    Jul 6 - Jul 12

    Hotel Hive + Flight

    Northwest
    6 nights
    3.5 star property
    9.2/10 - Wonderful (1,447 reviews)
    "Breakfast was perfect "
    Reviewed May 20, 2026
    Roundtrip • Tokyo (HND) - Washington (IAD)
    HND - IAD • 1 stop DCA - NRT • 1 stop
    ￥1,186,261
    ￥554,106
    per traveler
    found 9 hours ago
    Hotel Hive
  • Front of property - evening/night
    Jul 6 - Jul 12

    Sofitel Washington DC Lafayette Square + Flight

    Downtown Washington D.C.
    6 nights
    5.0 star property
    9.0/10 - Wonderful (1,193 reviews)
    "Location is great, our corner room was great, spacious, large bathroom, dinner and breakfast was excellent, valet parking was also great, convenient, our vehicle was ready within minutes when needed. We enjoyed our 2 days there and will return often."
    Reviewed May 19, 2026
    Roundtrip • Tokyo (HND) - Washington (IAD)
    HND - IAD • 1 stop DCA - NRT • 1 stop
    ￥1,260,582
    ￥590,612
    per traveler
    found 9 hours ago
    Sofitel Washington DC Lafayette Square
  • Exterior
    Jul 6 - Jul 12

    Eurostars Saint Gregory Dupont Circle Georgetown + Flight

    Downtown Washington D.C.
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,006 reviews)
    "Unexpected upgrade at check in. Was much appreciated!"
    Reviewed May 16, 2026
    Roundtrip • Tokyo (HND) - Washington (IAD)
    HND - IAD • 1 stop DCA - NRT • 1 stop
    ￥1,206,453
    ￥565,941
    per traveler
    found 9 hours ago
    Eurostars Saint Gregory Dupont Circle Georgetown

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
Aerial Panoramic View Annapolis Maryland State House Capital City

Historic District

2 out of top 10 points of interest in this area
5/5(85 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
The price is ￥18,407 per night from Jun 1 to Jun 2
￥18,407
￥26,425 total
Jun 1 - Jun 2
includes taxes & fees
9/10 Wonderful! (1,852 reviews)
"I wish there was a easier place to park, but it was a nice hotel"

Reviewed on May 19, 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 ￥17,415 per night from May 31 to Jun 1
￥17,415
￥19,854 total
May 31 - Jun 1
includes taxes & fees
DoubleTree by Hilton Hotel Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
Fully refundableReserve now, pay when you stay
The price is ￥18,134 per night from May 26 to May 27
￥18,134
￥20,673 total
May 26 - May 27
includes taxes & fees
Sonesta ES Suites Annapolis
See all 1,216 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 . 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

U.S. Naval Academy

4.5/5(450 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
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
Chesapeake Bay Bridge

Chesapeake Bay Bridge

4/5(273 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

Things to do

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

￥6,267
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Kent Narrows Sunset Cruise

Kent Narrows Sunset Cruise

￥6,268
per adult
Kent Narrows Sunset Cruise
Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

￥4,079
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.