Title: 4 Stars Hotels in Oyster Harbor, Annapolis from CA $165 - Find Cheap Oyster Harbor Hotels With 4 Stars | Expedia.ca [Oyster Harbor Travel Guide](https://expedia.ca/Annapolis-Oyster-Harbor.dx553248635976482330)[Vacation Rentals in Annapolis](https://expedia.ca/Annapolis-Vacation-Rentals.d6034082.Travel-Guide-VacationRentals)[Flights to Annapolis](https://expedia.ca/Cheap-Flights-To-Annapolis.d6034082.Travel-Guide-Flights)[Things to do in Annapolis](https://expedia.ca/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities)[Oyster Harbor Car Rentals](https://expedia.ca/Car-Rentals-In-Oyster-Harbor.d553248635976482330.Car-Rental-Guide)[Oyster Harbor Vacations](https://expedia.ca/Oyster-Harbor.d553248635976482330.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/1c03078f1f729b58cd71995ee5e48d7d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by KaiG # 4 Stars Hotels in Oyster Harbor, Annapolis from CA $165 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Oyster Harbor 4 Star Hotels Tonight [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976482330&startDate=2025-10-20&endDate=2025-10-21&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 21 - Oct 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976482330&startDate=2025-10-21&endDate=2025-10-22&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976482330&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976482330&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oyster Harbor 4 Star Hotels ![View from property](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/900/846/4033d0a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/900/846/237feb4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Graduate by Hilton Annapolis Annapolis 9.4/10 Exceptional (1014) "Staff was outstanding!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fred CA $217 CA $248 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/5575a0f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/3952dad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Annapolis Annapolis 8.6/10 Excellent (1021) "Comfortable place to stay, nice shopping area close by. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roya CA $145 CA $165 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner and brunch served](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/768e2886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/67adefe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/04365757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Annapolis Annapolis 8.6/10 Excellent (1007) "Would stay there again very soon " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $251 CA $286 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking, Balcony](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/af281015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/6d79f12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/f68fafe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Waterfront Hotel, Autograph Collection Historic District 8.8/10 Excellent (872) "Clean room. Friendly staff awesome location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brent CA $285 CA $325 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Superior Studio Suite | Balcony](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/d3121313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/ad8d4ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4750fa1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rod 'N' Reel Resort Chesapeake Beach 8.4/10 Very good (1003) "Great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maurie CA $139 CA $182 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/b42a3a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/d2860230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/9f06834f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club Stevensville 9.4/10 Exceptional (422) "Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rery CA $272 CA $337 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Full-size fridge, blender, toaster oven, waffle maker](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/1eac847e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | In-room dining](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/49f997cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/90332b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/48995b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Legacy Villa Upper Marlboro CA $231 CA $262 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Upper-Marlboro-Hotels-Legacy-Villa.h114870697.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Oyster-Harbor-Annapolis-Hotels.s40-n553248635976482330-0.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Oyster-Harbor-Annapolis-Hotels.s40-n553248635976482330-0.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Oyster Harbor. ![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Inn at Perry Cabin 308 Watkins Ln, St. Michaels, MD CA $567 CA $686 total Nov 12 - Nov 13 includes taxes & fees 9.4/10 Exceptional! (366 reviews) [](https://expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![The Inn at Tacaro Estate](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/ad846553_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Inn at Tacaro Estate 6220 Town Point Rd, Tracys Landing, MD CA $536 CA $612 total Oct 23 - Oct 24 includes taxes & fees 9.2/10 Wonderful! (10 reviews) [](https://expedia.ca/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) Still don't see what you're looking for? [See all properties in Oyster Harbor.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F10%2F2025&endDate=22%2F10%2F2025®ionId=553248635976482330&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F10%2F2025&endDate=22%2F10%2F2025®ionId=553248635976482330&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F10%2F2025&endDate=22%2F10%2F2025®ionId=553248635976482330&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F10%2F2025&endDate=22%2F10%2F2025®ionId=553248635976482330&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F10%2F2025&endDate=22%2F10%2F2025®ionId=553248635976482330&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=21%2F10%2F2025&endDate=22%2F10%2F2025®ionId=553248635976482330&star=40&star=40&amenities=WATER_PARK) 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. ## Top Oyster Harbor Hotel Reviews ![DoubleTree by Hilton Hotel Annapolis](//images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "It was healthy however I think the bagel could’ve been toasted longer." [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Graduate by Hilton Annapolis](//images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Staff was outstanding!" [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Clean room. Friendly staff awesome location. " [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![The Westin Annapolis](//images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg) ### The Westin Annapolis 10/10 Excellent "excellent service for our Remodelers Advantage Conference. Food was delicious and service to the rooms for snacks was great as well" [](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [1 Star Hotels in Holabird Industrial Park](https://www.expedia.ca/1Star-Holabird-Industrial-Park-Baltimore-Hotels.s10-n553248635976387003-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Cheltenham](https://www.expedia.ca/2Star-Cheltenham-Hotels.s20-0-d553248635975874284.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Graceland Park](https://www.expedia.ca/3Star-Graceland-Park-Baltimore-Hotels.s30-n553248635976385043-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Pleasant View Gardens](https://www.expedia.ca/3Star-Pleasant-View-Gardens-Baltimore-Hotels.s30-n553248635976385030-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Anchorage](https://www.expedia.ca/4Star-Anchorage-Annapolis-Hotels.s40-n553248635976473602-0.Travel-Guide-Filter-Hotels) - 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