Oyster Harbor, MD

Annapolis

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

Things to do

Annapolis Harbor and US Naval Academy Cruise

Annapolis Harbor and U.S. Naval Academy Cruise

$34
per adult
Annapolis Harbor and U.S. Naval Academy Cruise
Annapolis Chesapeake Bay Bridge Cruise

Annapolis Chesapeake Bay Bridge Cruise

$46
per adult
Annapolis Chesapeake Bay Bridge Cruise
Annapolis Scenic Severn River Cruise

Annapolis Scenic Severn River Cruise

$46
per adult
Annapolis Scenic Severn River Cruise
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

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

$10
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
The Original Haunted Pub Crawl by Annapolis Ghost Tours

The Original Haunted Pub Crawl by Annapolis Ghost Tours

$31
per adult
The Original Haunted Pub Crawl by Annapolis Ghost Tours
See all activities in Annapolis

Oyster Harbor Hotel Deals

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
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! (1,179 reviews)
"From the check in to the check out this was a great experience. The staff were super friendly and helpful, the room was clean and comfortable and the location was fantastic. Free and ample parking added to the pluses. This hotel is an Annapolis gem and we will definitely be staying there again."

Reviewed on Sep 16, 2026

DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$140 nightly
The price is $159 total per night from Oct 12 to Oct 13
$159 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! (2,002 reviews)
"Very impressed with the staff and all the help they provided for us.....! Cleanliness tops. My only complaint is with the cable TV quality. Very poor picture quality and cumbersome remote. This certainly requires a big upgrade. Also it wasn`t till the second day that I found electric outlets for ..."

Reviewed on Sep 16, 2026

Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
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 ...
8.8/10 Excellent! (1,016 reviews)
"Clerk was very informational, great room, Breakfast was only $18 each and filled us up! Great service and plenty of parking. Very much worth the value."

Reviewed on Sep 17, 2026

Crowne Plaza Annapolis by IHG
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
$149 nightly
The price is $170 total per night from Sep 27 to Sep 28
$170 total
Sep 27 - Sep 28
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
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
$132 nightly
The price is $146 total per night from Oct 18 to Oct 19
$146 total
Oct 18 - Oct 19
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)
"Nice weekend getaway"

Reviewed on Sep 16, 2026

Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
$89 nightly
The price is $98 total per night from Oct 18 to Oct 19
$98 total
Oct 18 - Oct 19
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)
"Front desk and breakfast staff were friendly and amazing. Breakfast had good a variety of options. Housekeeping staff was rude. Extra blanket was dirty, otherwise the room was clean. Early morning renovations and construction was loud and woke us up."

Reviewed on Sep 14, 2026

St Michaels Inn
See all 1,216 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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