Oyster Harbor Holidays from £740

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Your Oyster Harbour Holiday

Your next big journey is calling out to you with a holiday package to Oyster Harbour. Food, fun and nonstop great times — you're sure to find it in this neighbourhood. Some nearby attractions to check out during your trip to Oyster Harbour include Maryland Quiet Waters Park, Annapolis Maritime Museum and Annapolis Landing Marina. Stop dreaming and start doing. When it's time to lock in your next holiday to Oyster Harbour, Expedia will help you get there.

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
Price was £778, price is now £740 per person
£740
per person
30 Oct - 2 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Baltimore (BWI)
8.6/10 Excellent! (1,000 reviews)
Where is the receipt

Reviewed on 19 Aug 2025

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
Price was £1,052, price is now £909 per person
£909
per person
30 Oct - 2 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Baltimore (BWI)
9.4/10 Exceptional! (1,002 reviews)
Great location and fun hotel theme! Very nice staff. Walked to shops and food - loved Boatyard Restaurant. Thank you!

Reviewed on 20 Aug 2025

The Westin Annapolis

The Westin Annapolis

4 out of 5
Price was £1,000, price is now £893 per person
£893
per person
30 Oct - 2 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Baltimore (BWI)
8.6/10 Excellent! (1,005 reviews)
Bed was extremely comfortable. The Westin had great food at very reasonable prices.

Reviewed on 18 Aug 2025

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
Historic District
Price was £1,127, price is now £1,074 per person
£1,074
per person
30 Oct - 2 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Baltimore (BWI)
8.8/10 Excellent! (850 reviews)
The handicap accommodation suite was nice. The walk in shower and bench made our stay very comfortable. Our suite had a great view of luxury yachts and boats! Also, ordering breakfast from Choptank by using the QR code was convenient. Received breakfast in 15-20 minutes. We were impressed! See you next time!

Reviewed on 18 Aug 2025

Residence Inn by Marriott - Silver Spring

Residence Inn by Marriott - Silver Spring

3 out of 5
Price was £809, price is now £764 per person
£764
per person
14 Oct - 17 Oct
found 1 day ago
Return direct flight included
London (LGW) to Baltimore (BWI)
9/10 Wonderful! (541 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 17 Aug 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 featuring a city and street scenes as well as a small group of people

Historic District

1 out of top 10 points of interest in this area

While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.

Find hotels in Historic District

Top hotels in Oyster Harbor

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! (1,831 reviews)
"The location was wonderful. The hotel is quaint and a lovely place to stay. I only interacted with the front desk staff but she was very kind. I’m excited to come back."

Reviewed on 17 Aug 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 £136 per night from 2 Sept to 3 Sept
£136
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (1,011 reviews)
"Great location and fun hotel theme! Very nice staff. Walked to shops and food - loved Boatyard Restaurant. Thank you!"

Reviewed on 20 Aug 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 £82 per night from 27 Aug to 28 Aug
£82
27 Aug - 28 Aug
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"It was good."

Reviewed on 19 Aug 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,211 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Oyster Harbour travel package cost?
Get ready to book, because a getaway to Oyster Harbour starts from just £740. When you bundle your flights, hotels and car rentals into a package, you'll score the best prices.
If I'm not able to travel, can I cancel my Oyster Harbour travel package?
Don't worry if you're rethinking your Oyster Harbour travel package — you can cancel or amend your booking. And if you've booked it within 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 understand life can sometimes throw you a curveball, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we're ready to help.
How do I get a cheap travel package to Oyster Harbour?
Bundle your bookings with Expedia to save big on your next adventure. With over 550 air carriers and 1,000,000 hotels throughout the world, your Oyster Harbour travel package can be tailored exactly to suit your travel style. With all that extra cash, why not add a few interesting tours and activities? It's an easy way to unlock even more discounts. Your dream getaway to Oyster Harbour is much closer than you thought!
Does Expedia offer Book Now, Pay Later Oyster Harbour holidays?
We sure do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in instalments. Simply select the payment plan best suited to your needs during the checkout process and take away the stress of budgeting for your next trip. Be sure to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: Klarna offers manageable monthly payment plans that suit all budgets, so you can have that well-earned holiday now.
  • Pay in instalments holidays: If you want to pay off your getaway across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you spot an incredible deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you get what you want.

Where should I stay in Oyster Harbour?
Visitors come from every corner of the globe to experience U.S. Naval Academy and Maryland State House in Oyster Harbour. Book a room close to these terrific attractions and visit them whenever you want.
What are the top hotels in Oyster Harbour?
Make a reservation at Graduate Annapolis. It's one of the area's most sought-after properties. Another reputable option in Oyster Harbour is Historic Inns of Annapolis.
How far in advance should I book my Oyster Harbour holiday?
Reward yourself with the widest variety and the cheapest prices by booking your holiday to Oyster Harbour early. Airlines typically publish tickets around a year prior to departure, so reserve your spot as soon as possible. That said, Expedia is committed to giving you the best deals around, so there's never a bad time to book your dream holiday!
What does an Expedia Oyster Harbour travel package include?
That depends on what you're looking for. If you're travelling by yourself, you might decide to bundle flights and hotels. Taking the whole family to Oyster Harbour? A travel package including hotels, flights and rental cars might suit you better. Expedia gives you the freedom to build your own travel package.
What should I know before booking an Oyster Harbour travel package?
Bundling your bookings into an Oyster Harbour travel package is the most convenient way to organise your trip. Not only that, you'll get great discounts just for combining your flights, hotels and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with an Oyster Harbour Expedia travel package?
You certainly can. We offer more than 550 airline partners around the world, so go with the carrier that fits your travel preferences.

Popular places to visit

U.S. Naval Academy showing interior views, heritage architecture and military items

U.S. Naval Academy

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
Maryland Quiet Waters Park which includes a garden

Maryland Quiet Waters Park

Stroll along miles of trails through grassy parkland, hardwood forests and riverfront promenades and check out the visitor center at this pretty park.

Maryland Quiet Waters Park

Things to do

Food Tour Plate

Historic Annapolis Food Tour

£59
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

£19
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

£30
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. Flight-inclusive packages are ATOL protected.