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
The price is NT$3,151 per night from Aug 30 to Aug 31
NT$3,151
NT$3,592 total
Aug 30 - Aug 31
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 ...
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$2,960 per night from Aug 27 to Aug 28
NT$2,960
NT$4,477 total
Aug 27 - Aug 28
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 ...
9/10 Wonderful! (1,950 reviews)
"Staff was lovely and the location can’t be beat. The Maryland Inn building is old, and some of the elements are thus seemingly harder to clean (ie if you’re weird about bathrooms being spotless, this one isn’t for you)."

Reviewed on 2026/8/12

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$3,544 per night from Sep 1 to Sep 2
NT$3,544
NT$4,040 total
Sep 1 - Sep 2
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! (1,020 reviews)
"We had a great time at this hotel. Room was clean and cozy we spent time in the pool which did look bigger in the pictures but we still had fun. I would definitely stay again."

Reviewed on 2026/8/10

Crowne Plaza Annapolis by IHG
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
The price is NT$6,137 per night from Aug 24 to Aug 25
NT$6,137
NT$7,885 total
Aug 24 - Aug 25
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
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
The price is NT$4,201 per night from Aug 23 to Aug 24
NT$4,201
NT$4,789 total
Aug 23 - Aug 24
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 ...
9.4/10 Exceptional! (1,016 reviews)
"Location, staff and cleanliness were above and beyond!"

Reviewed on 2026/8/11

Graduate by Hilton Annapolis
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
The price is NT$2,877 per night from Aug 31 to Sep 1
NT$2,877
NT$3,165 total
Aug 31 - Sep 1
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 ...
8.2/10 Very Good! (1,001 reviews)
"The room was fine. Was only provided a 1/4 roll of toilet paper. Breakfast was included with the price but not good. Coffee thick as mud. Staff nice and accommodating."

Reviewed on 2026/8/11

St Michaels Inn
See all 1,210 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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