Oyster Harbor Travel Guide
Tourist Guide
Visit Oyster Harbor
Activities
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
NZ$52
per adult
Annapolis Harbor and U.S. Naval Academy Cruise
NZ$59
per adult
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
NZ$17
per traveller
80% of travellers recommend
Our pick of the best Oyster Harbor Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is NZ$189 per night from 30 Aug to 31 Aug
NZ$189
per night
30 Aug - 31 Aug
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 ...
8.8/10 Excellent! (1,093 reviews)
"Room was clean. Staff were friendly. The area shuttle was a wonderful amenity to have access to with friendly drivers! The no my opportunity to note is the air conditioning was inconsistent getting very cold then cycling off to very warm making it hard to sleep comfortably during a summer stay."
Reviewed on 11 Aug 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is NZ$236 per night from 25 Aug to 26 Aug
NZ$236
per night
25 Aug - 26 Aug
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 ...
9/10 Wonderful! (1,945 reviews)
"Our stay was overall good. The room stayed cool during a very hot weekend. It is so conveniently located! Our only opportunity to note is that our housekeeping was inconsistent. Day 2 we were in the room and we asked if the house keeper could come back. They never came back. Day 3 the house keeper ..."
Reviewed on 11 Aug 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
The price is NZ$213 per night from 1 Sept to 2 Sept
NZ$213
per night
1 Sept - 2 Sept
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! (1,020 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 10 Aug 2026
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
The price is NZ$405 per night from 17 Aug to 18 Aug
NZ$405
per night
17 Aug - 18 Aug
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 ...
8.6/10 Excellent! (1,018 reviews)
"Service"
Reviewed on 11 Aug 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
The price is NZ$252 per night from 31 Aug to 1 Sept
NZ$252
per night
31 Aug - 1 Sept
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 ...
St Michaels Inn
1228 S Talbot Street St. Michaels MD
The price is NZ$160 per night from 31 Aug to 1 Sept
NZ$160
per night
31 Aug - 1 Sept
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 ...
8.2/10 Very good! (1,000 reviews)
"We enjoyed our stay. Rooms were clean and the staff were very friendly. Looking forward to our next visit to St Michael’s. We would definitely stay here again."
Reviewed on 11 Aug 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.
Our guide on 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.
