Oyster Harbor, MD

Annapolis

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

Oyster Harbor Hotel Deals

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is NT$3,077 per night from Sep 29 to Sep 30
NT$3,077
NT$3,507 total
Sep 29 - Sep 30
includes taxes & 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! (1,201 reviews)
"I liked the staff!"

Reviewed on 2026/9/25

DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
The price is NT$3,377 per night from Oct 4 to Oct 5
NT$3,377
NT$4,935 total
Oct 4 - Oct 5
includes taxes & 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
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
The price is NT$3,493 per night from Oct 4 to Oct 5
NT$3,493
NT$3,982 total
Oct 4 - Oct 5
includes taxes & 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! (1,013 reviews)
"This was my and my Wife’s first time here in this area … we bought tickets for renaissance festival and decided to come in a day earlier … we initially choose a different hotel for a visit but then decided to go to the crowne plaza for the awesome pool and what looked like a skyline horizon from ..."

Reviewed on 2026/9/26

Crowne Plaza Annapolis by IHG
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
The price is NT$4,661 per night from Oct 26 to Oct 27
NT$4,661
NT$5,314 total
Oct 26 - Oct 27
includes taxes & 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
The price is NT$4,591 per night from Oct 7 to Oct 8
NT$4,591
NT$6,154 total
Oct 7 - Oct 8
includes taxes & 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
The price is NT$2,829 per night from Oct 4 to Oct 5
NT$2,829
NT$3,112 total
Oct 4 - Oct 5
includes taxes & 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! (1,007 reviews)
"our welcome was not pleasant. the executive queen room was okay but bedding could have been better and the pull out sofa was not made up. stayed here many times but the place can use some freshening up."

Reviewed on 2026/9/27

St Michaels Inn
See all 1,229 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 Ballet Theater of Maryland and Spa Creek.

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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