Oyster Harbor, MD

Annapolis

A sunset over a calm sea with a pier extending into the water.

Explore the historic sites, coastal views, and community charm surrounding Oyster Harbor for a memorable family getaway.

Oyster Harbor is an ideal destination for outdoor, family travelers. Nearby, you can visit Annapolis Landing Marina for a relaxing day on the water or explore the historic Hammond-Harwood House and the Maryland State House, both steeped in local history. There are various activities to engage in, including shopping at the Bay Bridge Market Place Shopping Center, playing a round of golf at Annapolis Golf Club, or catching a game at the Navy-Marine Corps Memorial Stadium. For nature enthusiasts, nearby Gibson Island offers scenic views, while the Eastern Shore and Kent Island provide beautiful coastal experiences.

Make sure to explore the distinct neighborhoods surrounding Oyster Harbor. Hillsmere Shores and Annapolis are known for outdoor, family experiences, with highlights like Sandy Point State Park and the Annapolis Maritime Museum. Additionally, Highland Beach is recognized for its outdoor, beach experiences, offering a more relaxed atmosphere for visitors. Each of these areas provides unique opportunities to engage with the local community and enjoy the natural surroundings.

The best time to visit Oyster Harbor is from June to September when the weather is warm, mostly dry, and often sunny. These months are ideal for outdoor activities and family outings, although they can also be the busiest. If you prefer a quieter experience, consider visiting during the early spring or late fall when you can still enjoy the area's beauty without the larger crowds typical of summer.


Things to do


Oyster Harbor Hotel Deals

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$106 nightly
The price is $120 total per night from Dec 3 to Dec 4
$120 total
Dec 3 - Dec 4
Total with taxes and fees
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (2,071 reviews)
"The stay was so nice, the room had charm, it was large, unique, quaint and romantic. Staff was super friendly, definitely recommend!!"

Reviewed on Nov 11, 2026

Historic Inns of Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
$172 nightly
The price is $191 total per night from Nov 30 to Dec 1
$191 total
Nov 30 - Dec 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants, and a marina. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,001 reviews)
"Our stay was for several days. The property is very well maintained, and great views of Chesapeake Bay. Booking through Expedia is the best decision because the daily rack rate is far higher. There is onsite uniformed security. There are an abundance of handicapped parking and a parking garage. We ..."

Reviewed on Nov 10, 2026

Rod 'N' Reel Resort
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
$110 nightly
The price is $125 total per night from Nov 15 to Nov 16
$125 total
Nov 15 - Nov 16
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Crowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
$85 nightly
The price is $97 total per night from Nov 23 to Nov 24
$97 total
Nov 23 - Nov 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Sonesta ES Suites Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$89 nightly
The price is $102 total per night from Nov 23 to Nov 24
$102 total
Nov 23 - Nov 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.8/10 Excellent! (1,274 reviews)
"Great place……………………………….."

Reviewed on Nov 11, 2026

DoubleTree by Hilton Hotel Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
$215 nightly
The price is $245 total per night from Nov 23 to Nov 24
$245 total
Nov 23 - Nov 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
8.8/10 Excellent! (1,001 reviews)
"Over priced"

Reviewed on Nov 11, 2026

Annapolis Waterfront Hotel, Autograph Collection
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.

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
Learn more about Oyster Harbor

Historic District

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

Eastport

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

Murray Hill

While visiting Murray Hill, you might make a stop by sights like Spa Creek and Ballet Theater of Maryland.

Hillsmere

If you're spending some time in Hillsmere, Maryland Quiet Waters Park and Great Frogs Winery are top sights worth seeing.

Cape Saint Claire

If you're spending some time in Cape Saint Claire, Northern Chesapeake Bay and Chesapeake Bay are top sights worth seeing.



Oyster Harbor, MD

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