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
The Original Haunted Pub Crawl by Annapolis Ghost Tours
$31
per adult
Oyster Harbor Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$83 nightly
The price is $95 total per night from Sep 27 to Sep 28
$95 total
Sep 27 - Sep 28
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! (1,170 reviews)
"This hotel is dated. The carpets are worn and stained in spots. The towels in the room were very worn. The windows did not block the noise from the highway near the hotel. The curtains would not open properly. The bedding and surfaces were clean. This hotel needs upgrading."
Reviewed on Sep 13, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
$141 nightly
The price is $160 total per night from Oct 12 to Oct 13
$160 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! (1,993 reviews)
"Property was a historical renovation which is very well done. Best part was location. A bit pricey and we didn’t need or use the complimentary bottle of wine. Bottled water would have been preferred. Staff and housekeeping was great. Coffee was available, but no food service for breakfast."
Reviewed on Sep 12, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$110 nightly
The price is $125 total per night from Sep 27 to Sep 28
$125 total
Sep 27 - Sep 28
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 ...
Graduate by Hilton Annapolis
126 West St Annapolis MD
$155 nightly
The price is $177 total per night from Oct 1 to Oct 2
$177 total
Oct 1 - Oct 2
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)
"Great stay- Go Navy Beat Army!"
Reviewed on Sep 12, 2026
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
$163 nightly
The price is $181 total per night from Oct 11 to Oct 12
$181 total
Oct 11 - Oct 12
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
$86 nightly
The price is $95 total per night from Sep 15 to Sep 16
$95 total
Sep 15 - Sep 16
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! (1,012 reviews)
"Well, it was a nice hotel and the price was reasonable, but it’s a little rundown the rooms inside a very nice, but the overall property is certainly not pretty. The other thing is it’s kind of a mix between nice and not so nice. Breakfast was less than average coffee was weak and not that good but ..."
Reviewed on Sep 12, 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.
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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