Oyster Harbor Trip

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Price found within the past 48 hours. Click for updated prices.
Sheraton Pentagon City Hotel

Sheraton Pentagon City Hotel

3.5 out of 5
Price was ₹71,325, price is now ₹71,325 per person
₹71,325
per person
15 Mar - 19 Mar
found 5 hours ago
Return flight included
Chicago (ORD) to Baltimore (BWI)
8.4/10 Very Good! (2,804 reviews)
The hotel and room were very nice. However, we stood in the cold for a long time waiting for a shuttle that never arrived (“due to bad weather”). & shuttles in AM start at 6 am, so too late to take due to early AM.

Reviewed on 27 Jan 2026

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Price was ₹93,524, price is now ₹73,996 per person
₹73,996
per person
15 Mar - 19 Mar
found 5 hours ago
Return flight included
Chicago (ORD) to Baltimore (BWI)
9.4/10 Exceptional! (1,603 reviews)
Great service and loved my room!

Reviewed on 24 Jan 2026

Hyatt Place Arlington/Courthouse Plaza

Hyatt Place Arlington/Courthouse Plaza

3 out of 5
Court House
Price was ₹85,332, price is now ₹73,035 per person
₹73,035
per person
15 Mar - 19 Mar
found 5 hours ago
Return flight included
Chicago (ORD) to Baltimore (BWI)
9.2/10 Wonderful! (1,004 reviews)
Clean room, and spacious bathroom. Very friendly concierge and great customer service.

Reviewed on 23 Jan 2026

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
Beautiful troll downtown Annapolis... #Adventure

Historic District

2 out of top 10 points of interest in this area

While visiting Historic District, you might make a stop by sights like Thurgood Marshall Memorial and Maryland State House.

Find hotels in Historic District

Top hotels in Oyster Harbor

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 ₹13,659 per night from 15 Feb to 16 Feb
₹13,659
₹15,571 total
15 Feb - 16 Feb
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
Hotel is obviously not new. However it is very well maintained, very clean and we had a pleasant stay. Staff were professional and polite and allowed us an early checkin. Onsite restaurant was pretty good as well. Would stay again.

Reviewed on 21 Jan 2026

Graduate by Hilton Annapolis
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 ₹13,159 per night from 1 Feb to 2 Feb
₹13,159
₹18,147 total
1 Feb - 2 Feb
includes taxes & fees
9/10 Wonderful! (1,905 reviews)
We had a wonderful stay at this here. The staff were incredibly accommodating, the room was clean and well-maintained, and the location was perfect. We would stay again

Reviewed on 25 Jan 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 ₹7,000 per night from 8 Feb to 9 Feb
₹7,000
₹7,980 total
8 Feb - 9 Feb
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
Staff was very friendly. Made check in quick and enjoyable

Reviewed on 24 Jan 2026

DoubleTree by Hilton Hotel Annapolis
See all 1,210 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 Harbour holiday package cost?
Create unforgettable memories with our Oyster Harbour holiday packages, which start from only ₹71,325. 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 Harbour?
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 Harbour holiday 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 holiday in Oyster Harbour is much closer than you thought!
Where should I stay in Oyster Harbour?
Most people who travel to Oyster Harbour 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 Harbour?
Reserve a room at Waterfront Chesapeake Cottage In Oyster Bay. It's one of this neighbourhood's most in-demand properties. Another top-rated option in Oyster Harbour is Cosy Cottage By The Beach - Waterviewminutes From Downtown Annapolis.
How far in advance should I book my Oyster Harbour holiday?
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 Harbour sometimes occur a few weeks before the date of departure.
What does an Expedia Oyster Harbour travel package include?
With Expedia, you can select a combination of hotels, flights and car rentals to create your ideal Oyster Harbour 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 Harbour 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 holiday is only a few clicks away.
Can I choose my airline with an Oyster Harbour Expedia holiday 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 Harbour holiday package?
Don't worry if you're rethinking your Oyster Harbour holiday 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.

Popular places to visit

Chesapeake Bay Bridge

Chesapeake Bay Bridge

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
Kunta Kinte–Alex Haley Memorial

Kunta Kinte–Alex Haley Memorial

This moving memorial marks the spot where Kunta Kinte, the ancestor of author Alex Haley, was brought from Africa and sold into slavery.

Kunta Kinte–Alex Haley Memorial
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.