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
$86 nightly
The price is $98 total per night from Sep 27 to Sep 28
$98 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 ...
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! (1,999 reviews)
"Everyone was polite and the room was extremely quiet. It was relaxing. My daughter and I enjoyed staying at the Historic Inns of Annapolis."

Reviewed on Sep 18, 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 ...
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
$133 nightly
The price is $148 total per night from Oct 13 to Oct 14
$148 total
Oct 13 - Oct 14
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 ...
Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
$95 nightly
The price is $105 total per night from Sep 20 to Sep 21
$105 total
Sep 20 - Sep 21
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! (1,001 reviews)
"I am very hard pressed to recommend this hotel to anyone - biggest issue was cleanliness. This summarizes my conversation with manager at check out. Their response: NO payment adjustment - booked thru 3rd party. The only plus for this Inn was its proximity to St. Michaels’ town center, noting that ..."

Reviewed on Sep 17, 2026

St Michaels Inn
See all 1,231 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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