Oyster Harbor, MD
Annapolis
Visit Oyster Harbor
Things to do
Annapolis Harbor and U.S. Naval Academy Cruise
$34
per adult
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
$10
per traveler
80% of travellers recommend
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
$30
per adult
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
$36
per adult
Oyster Harbor Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$90 nightly
The price is $103 total per night from Oct 4 to Oct 5
$103 total
Oct 4 - Oct 5
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! (1,215 reviews)
"Very clean"
Reviewed on Sep 30, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
$148 nightly
The price is $169 total per night from Oct 12 to Oct 13
$169 total
Oct 12 - Oct 13
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! (2,027 reviews)
"The best news about this hotel is the location - just a couple of mins walk to Main St so it's very convenient. Parking is tricky but that's Annapolis! The hotel is obviously an old building but is mostly well decorated and maintained. I was very disappointed that there was no bar / restaurant as ..."
Reviewed on Sep 29, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$110 nightly
The price is $125 total per night from Oct 4 to Oct 5
$125 total
Oct 4 - Oct 5
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 ...
8.8/10 Excellent! (1,019 reviews)
"Pool was green and hot tub was empty. Our room's toilet seat was loose. And the first night there was no parking (we had to park in a bank parking lot) because they were hosting an event."
Reviewed on Sep 29, 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $167 total per night from Oct 26 to Oct 27
$167 total
Oct 26 - Oct 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.4/10 Exceptional! (1,014 reviews)
"V"
Reviewed on Sep 29, 2026
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
$162 nightly
The price is $180 total per night from Oct 8 to Oct 9
$180 total
Oct 8 - Oct 9
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 ...
St Michaels Inn
1228 S Talbot Street St. Michaels MD
$99 nightly
The price is $109 total per night from Oct 4 to Oct 5
$109 total
Oct 4 - Oct 5
Total with taxes and fees
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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.
Admiral Heights
Admiral Heights might not have many top sights, but Navy-Marine Corps Memorial Stadium and Maryland Hall for Creative Arts are two attractions nearby that you can check out.
Oyster Harbor, MD
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