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
Oyster Harbor Hotel Deals
Graduate by Hilton Annapolis
126 West St Annapolis MD
$155 nightly
The price is $177 total per night from Nov 11 to Nov 12
$177 total
Nov 11 - Nov 12
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 ...
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$98 nightly
The price is $111 total per night from Oct 25 to Oct 26
$111 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
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $146 total per night from Nov 5 to Nov 6
$146 total
Nov 5 - Nov 6
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! (1,000 reviews)
"Loved the balcony."
Reviewed on Oct 19, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$110 nightly
The price is $125 total per night from Oct 25 to Oct 26
$125 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 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 ...
9/10 Wonderful! (2,052 reviews)
"Had a wonderful stay, property could use a couple vending machine between floors."
Reviewed on Oct 20, 2026
St Michaels Inn
1228 S Talbot Street St. Michaels MD
$89 nightly
The price is $98 total per night from Nov 1 to Nov 2
$98 total
Nov 1 - Nov 2
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! (1,000 reviews)
"Staff was exceptional. Historical vibe was fun and coastal-appropriate. Close to DC and other fun destinations."
Reviewed on Oct 19, 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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