Oyster Harbor, MD
Annapolis
Visit Oyster Harbor
Things to do
Annapolis Harbor and U.S. Naval Academy Cruise
$34
per adult
Best of Annapolis Tour: Colonial, State House, Naval Academy
$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
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$98 nightly
The price is $111 total per night from Sep 27 to Sep 28
$111 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! (1,147 reviews)
"."
Reviewed on Aug 31, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $168 total per night from Sep 29 to Sep 30
$168 total
Sep 29 - Sep 30
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! (1,985 reviews)
"I really wanted to love this place, but alas there were problems. First of all, the financial: Valet parking required our prepaying. We used our car on our last evening and self-parked after being assured by the attendant we would be reimbursed for that night. When we checked out, another attendant ..."
Reviewed on Aug 31, 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
$153 nightly
The price is $175 total per night from Sep 13 to Sep 14
$175 total
Sep 13 - Sep 14
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 ...
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
$191 nightly
The price is $212 total per night from Oct 1 to Oct 2
$212 total
Oct 1 - Oct 2
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 ...
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$103 nightly
The price is $117 total per night from Sep 30 to Oct 1
$117 total
Sep 30 - Oct 1
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 ...
8.6/10 Excellent! (1,008 reviews)
"Pool is open but not clean and hot tub is under maintenance, which is not stated anywhere until you actually head to the pool area"
Reviewed on Aug 31, 2026
St Michaels Inn
1228 S Talbot Street St. Michaels MD
$86 nightly
The price is $95 total per night from Sep 9 to Sep 10
$95 total
Sep 9 - Sep 10
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! (1,016 reviews)
"Parking was convenient, didn't have to carry luggage very far. Staff was very friendly and helpful. The lady in the breakfast area was exceptional. Pool was very clean, could use more seats."
Reviewed on Aug 31, 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 Ballet Theater of Maryland and Spa Creek.
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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