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$3,085 per night from Sep 27 to Sep 28
NT$3,085
NT$3,517 total
Sep 27 - Sep 28
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! (1,144 reviews)
"Clean room ,nice helpful staff and the shuttle service was 👍 great"

Reviewed on 2026/8/31

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$3,348 per night from Sep 27 to Sep 28
NT$3,348
NT$4,898 total
Sep 27 - Sep 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! (1,982 reviews)
"Location, cleanliness, price, friendliness of the staff. Love it there. Only place we stay when visiting Annapolis."

Reviewed on 2026/8/30

Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
The price is NT$4,842 per night from Sep 13 to Sep 14
NT$4,842
NT$5,519 total
Sep 13 - Sep 14
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$4,572 per night from Oct 1 to Oct 2
NT$4,572
NT$6,127 total
Oct 1 - Oct 2
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 ...
8.6/10 Excellent! (1,010 reviews)
"The resort was clean, and the rooms were modern, comfortable, and well maintained. There were several restaurants on the property, along with a mini casino, which provided plenty of dining and entertainment options. The staff was friendly and welcoming."

Reviewed on 2026/8/31

Rod 'N' Reel Resort
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
The price is NT$3,067 per night from Sep 13 to Sep 14
NT$3,067
NT$3,496 total
Sep 13 - Sep 14
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 ...
8.6/10 Excellent! (1,006 reviews)
"The hotel was immaculate and the staff were incredibly helpful. However, my room was on the back of the hotel, overlooking the highway, and noise from the traffic interrupted my sleep. I would suggest requesting a room away from this area."

Reviewed on 2026/8/31

Crowne Plaza Annapolis by IHG
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
The price is NT$2,988 per night from Sep 1 to Sep 2
NT$2,988
NT$3,287 total
Sep 1 - Sep 2
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! (1,013 reviews)
"Head guy at front entrance is rude and not a happy guy"

Reviewed on 2026/8/30

St Michaels Inn
See all 1,222 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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