Oyster Harbor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Jul 1 - Jul 6

    The Normandy Hotel + Flight

    Northwest
    5 nights
    3.0 star property
    8.6/10 - Excellent (1,000 reviews)
    "Nice and quiet. Small rooms and much older hotel, but some rooms may be bigger if you pay more I’m not sure. It does show some signs of aging but that didn’t bother me at all. The breakfast good quality and all I need. All the options were fairly healthy although they ran out of boiled eggs quick every morning! Free coffee always ready whenever, love that. They also did a free wine hour from 6-7p, which was just nice to have offered. Staff were professional and personable. I probably won’t stay..."
    Reviewed May 16, 2026
    Roundtrip • Toronto (YTZ) - Washington (IAD)
    YTZ - IAD • Nonstop IAD - YTZ • Nonstop
    CA $1,541
    CA $1,055
    per traveller
    found 1 day ago
    The Normandy Hotel
  • Exterior
    Aug 1 - Aug 6

    Salamander Washington DC + Flight

    Southwest
    5 nights
    5.0 star property
    9.4/10 - Exceptional (1,090 reviews)
    "My family had a great stay at the Salamander DC. The staff was very friendly and the property was beautiful. The pool was clean and water temperature was comfortable. We would definitely stay here again. "
    Reviewed May 19, 2026
    Roundtrip • Toronto (YTZ) - Washington (IAD)
    YTZ - IAD • Nonstop IAD - YTZ • Nonstop
    CA $2,008
    CA $1,374
    per traveller
    found 18 hours ago
    Salamander Washington DC
  • Exterior
    Aug 1 - Aug 6

    Club Wyndham National Harbor + Flight

    Oxon Hill
    5 nights
    3.5 star property
    8.4/10 - Very good (483 reviews)
    "Courteous "
    Reviewed April 29, 2026
    Roundtrip • Toronto (YTZ) - Washington (IAD)
    YTZ - IAD • Nonstop IAD - YTZ • Nonstop
    CA $2,216
    CA $1,538
    per traveller
    found 18 hours ago
    Club Wyndham National Harbor
  • Indoor pool, outdoor pool, pool umbrellas, sun loungers
    Jul 21 - Jul 24

    Rosewood Washington, D.C. + Flight

    Northwest
    3 nights
    5.0 star property
    9.2/10 - Wonderful (205 reviews)
    "The property is older, has smaller rooms, worn public spaces and not special but charges like it’s the a brand new Ritz or Four seasons. It does not deserve the four stars. "
    Reviewed April 14, 2026
    Roundtrip • Montreal (YUL) - Washington (IAD)
    YUL - IAD • 1 stop IAD - YUL • 1 stop
    CA $2,443
    CA $1,704
    per traveller
    found 1 day ago
    Rosewood Washington, D.C.
  • Lobby
    Jul 1 - Jul 6

    Fairmont Washington, D.C., Georgetown + Flight

    Northwest
    5 nights
    5.0 star property
    9.4/10 - Exceptional (1,002 reviews)
    "If you're looking at this hotel, go ahead and book it! Not only is it luxurious and friendly, but you'll find at least 5 taxis by it at any time (a definite plus when certain Metro lines are being repaired). Added bonus: the signature house fragrance is unspeakably delicious. You will love your stay here!"
    Reviewed April 29, 2026
    Roundtrip • Toronto (YTZ) - Washington (IAD)
    YTZ - IAD • Nonstop IAD - YTZ • Nonstop
    CA $2,430
    CA $1,723
    per traveller
    found 1 day ago
    Fairmont Washington, D.C., 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

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 $159 per night from Jun 1 to Jun 2
CA $159
CA $228 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 CA $150 per night from May 31 to Jun 1
CA $150
CA $172 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 CA $157 per night from May 25 to May 26
CA $157
CA $179 total
May 25 - May 26
includes taxes & fees
Sonesta ES Suites Annapolis
See all 1,208 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 . 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(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
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
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

Things to do

Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

CA $36
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost 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
Historic Annapolis Food Tour

Historic Annapolis Food Tour

CA $109
per adult
Historic Annapolis Food 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.