Oyster Harbor, MD
Annapolis
Visit Oyster Harbor
Things to do
Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise
$34
per adult
90% of travellers recommend
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
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! (1,001 reviews)
"Extremely spacious, nicely appointed room."
Reviewed on Oct 18, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$114 nightly
The price is $130 total per night from Oct 25 to Oct 26
$130 total
Oct 25 - Oct 26
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 ...
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
$132 nightly
The price is $146 total per night from Oct 27 to Oct 28
$146 total
Oct 27 - Oct 28
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 ...
8.6/10 Excellent! (1,007 reviews)
"The first thing I noticed was hair on my sheets. I should have insisted on a sheet change, in hindsight but I used lint brush to remove. Later, after spilling water we had to use a towel to clean up. It was black once we cleaned. So gross, the floor didn't appear dirty but obviously it was. Nothing ..."
Reviewed on Oct 18, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$106 nightly
The price is $121 total per night from Nov 17 to Nov 18
$121 total
Nov 17 - Nov 18
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! (1,003 reviews)
"Elevators were often down to only one working. Very slow elevators long lines constantly. Restaraunt bar area has horrific service waited 30 minutes still never got service so had to leave and go next door. Front desk excuse is “hotel is old.” Imagine if Waldorf used that excuse."
Reviewed on Oct 18, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
$120 nightly
The price is $137 total per night from Nov 9 to Nov 10
$137 total
Nov 9 - Nov 10
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 ...
St Michaels Inn
1228 S Talbot Street St. Michaels MD
$79 nightly
The price is $87 total per night from Nov 19 to Nov 20
$87 total
Nov 19 - Nov 20
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 ...
8/10 Very Good! (1,006 reviews)
"The updates look nice and the paint looks good, however the bathroom was not clean. The shower/tub had hair and the floor was not clean in the corners. I was very disappointed"
Reviewed on Oct 18, 2026
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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