Oyster Harbor, MD

Annapolis

A sunset over a calm sea with a pier extending into the water.

Things to do

Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise

Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise

$34
per adult
90% of travellers recommend
Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise
Annapolis Harbor and U.S. Naval Academy Cruise

Annapolis Harbor and U.S. Naval Academy Cruise

$34
per adult
Annapolis Harbor and U.S. Naval Academy Cruise
Scenic Spa Creek Cruise of Annapolis

Scenic Spa Creek Cruise of Annapolis

$34
per adult
Scenic Spa Creek Cruise of Annapolis
Annapolis Sunset Cruise

Annapolis Sunset Cruise

$48
per adult
Annapolis Sunset Cruise
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

$9
per traveler
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

$30
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Annapolis

Oyster Harbor Hotel Deals

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
$139 nightly
The price is $158 total per night from Nov 22 to Nov 23
$158 total
Nov 22 - Nov 23
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 ...
Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$91 nightly
The price is $104 total per night from Nov 22 to Nov 23
$104 total
Nov 22 - Nov 23
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! (1,251 reviews)
"Esperaba mas de este hotel. Aun asi no esta mal."

Reviewed on Oct 20, 2026

DoubleTree by Hilton Hotel Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
$112 nightly
The price is $124 total per night from Nov 17 to Nov 18
$124 total
Nov 17 - Nov 18
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! (1,003 reviews)
"The Hotel was excellent. However, Expedia did not disclose that there was an additional charge for resort fee that was not included in the quoted price from Expedia. There was an additional $33.00 when I checked into the hotel. I could have gone with a different online reservation cheaper."

Reviewed on Oct 22, 2026

Rod 'N' Reel Resort
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
$103 nightly
The price is $117 total per night from Nov 22 to Nov 23
$117 total
Nov 22 - Nov 23
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! (1,005 reviews)
"We stayed for two nights and were very happy with the size and quality of the room. The buffet-Breakfast was excellent and included in the rate. A large shopping mall and several restaurants nearby."

Reviewed on Oct 21, 2026

Crowne Plaza Annapolis by IHG
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
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 ...
Historic Inns of Annapolis
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
$80 nightly
The price is $88 total per night from Nov 22 to Nov 23
$88 total
Nov 22 - Nov 23
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! (1,004 reviews)
"older facility but kept clean. a good value for an over night"

Reviewed on Oct 22, 2026

St Michaels Inn
See all 1,230 properties in Oyster Harbor
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
An aerial view of a coastal town with a prominent church, dense residential area, and a marina with boats.

Historic District

While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.

A marina with numerous sailboats docked, surrounded by residential houses and a backdrop of trees and a distant shoreline.

Eastport

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

A cityscape with historic buildings, a river, and a bridge in the background.

Murray Hill

While visiting Murray Hill, you might make a stop by sights like Spa Creek and Ballet Theater of Maryland.

A large suspension bridge spanning a wide river at sunset.

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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