Oyster Harbor Travel Guide
Annapolis
Visit Oyster Harbor
Top hotels in Oyster Harbor
Graduate by Hilton Annapolis
126 West St Annapolis MD
The price is 3.799.400 ₫ per night from 26 Oct to 27 Oct
3.799.400 ₫
4.331.316 ₫ total
26 Oct - 27 Oct
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the bar and the helpful ...
9.4/10 Exceptional! (1,000 reviews)
"Clean room, very nice decor and great staff"
Reviewed on 16 Oct 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is 2.865.470 ₫ per night from 20 Oct to 21 Oct
2.865.470 ₫
3.266.635 ₫ total
20 Oct - 21 Oct
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
The price is 3.742.582 ₫ per night from 27 Oct to 28 Oct
3.742.582 ₫
4.154.266 ₫ total
27 Oct - 28 Oct
includes taxes & fees
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 the clean ...
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
The price is 2.743.810 ₫ per night from 15 Nov to 16 Nov
2.743.810 ₫
3.127.943 ₫ total
15 Nov - 16 Nov
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,002 reviews)
"Do not stay here if you are seeking a restful, quiet night. My room was on the highway and we were startled and disturbed by semitrucks all night. The staff explained they were not able to move me as the hotel was fully booked."
Reviewed on 17 Oct 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is 2.217.827 ₫ per night from 30 Oct to 31 Oct
2.217.827 ₫
3.413.590 ₫ total
30 Oct - 31 Oct
includes taxes & fees
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
St Michaels Inn
1228 S Talbot Street St. Michaels MD
The price is 2.073.388 ₫ per night from 1 Nov to 2 Nov
2.073.388 ₫
2.280.726 ₫ total
1 Nov - 2 Nov
includes taxes & fees
Stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8/10 Very good! (1,001 reviews)
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing ..."
Reviewed on 16 Oct 2026
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 for the activities you enjoy most.
Historic District
While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.
Eastport
While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.
Murray Hill
If you're spending some time in Murray Hill, Spa Creek and Ballet Theater of Maryland are top sights worth seeing.
Hillsmere
While visiting Hillsmere, you might make a stop by sights like Maryland Quiet Waters Park and Great Frogs Winery.
Cape Saint Claire
While visiting Cape Saint Claire, you might make a stop by sights like Northern Chesapeake Bay and Chesapeake Bay.
