Waterfront holiday rentals in Annapolis
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Top-rated waterfront rentals in Annapolis
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for waterfront rentals in Annapolis
Waterfront apartment rentals
Flat in Grasonville
4.89 out of 5 average rating, 175 reviewsHalcyon house. Lovely views on MD eastern shore.
17–24 Feb
Flat in Chester
4.97 out of 5 average rating, 234 reviewsCozy Waterfront Apartment Chester, MD
14–21 Dec
Flat in Essex
4.97 out of 5 average rating, 223 reviewsA place unique on sue creek
19–26 Nov
Flat in Deale
4.91 out of 5 average rating, 614 reviewsRomantic Wtrfrnt Flat+Solarium@Chesapeake Paradise
25 Jan – 1 Feb
Flat in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
30 Oct – 6 Nov
Flat in Alexandria
4.87 out of 5 average rating, 246 reviewsThe Duke Suite and Prince Street Inn
20–27 Oct
Flat in Annapolis
4.98 out of 5 average rating, 90 reviewsOne bedroom apartment in Annapolis
4–11 Nov
Flat in Pasadena
5.0 out of 5 average rating, 6 reviewsRelaxing Waterfront Apartment!
30 May – 6 Jun
Waterfront house rentals
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
27 Sept – 4 Oct
Home in Edgewater
4.98 out of 5 average rating, 100 reviewsLuxury Modern Home on Water+Hotub- Annapolis 25min
18–25 Jul
Home in Crownsville
4.94 out of 5 average rating, 148 reviewsSevern River Waterfront Home
29 Dec – 5 Jan
Home in Kent Narrows
5.0 out of 5 average rating, 279 reviewsChester Riverfront At Kent Narrows
16–23 Oct
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
13–20 Dec
Home in Annapolis
4.89 out of 5 average rating, 182 reviewsCountry House on the Bay
21–28 Aug
Home in Grasonville
4.94 out of 5 average rating, 226 reviewsRiver Front, Private Single Family Home
17–24 Nov
Home in Stevensville
4.94 out of 5 average rating, 196 reviews❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
26 Jan – 2 Feb
Waterfront apartment rentals
Apartment in Baltimore
4.9 out of 5 average rating, 176 reviewsHistoric Federal hills urban lifestyle
1–8 Jan
Apartment in Washington
4.83 out of 5 average rating, 18 reviewsHistorical Georgetown Modern Penthouse 12 min DCA
27 May – 3 Jun
Apartment in Annapolis
5.0 out of 5 average rating, 7 reviewsCharming Annapolis Waterfront Condo
24 Sept – 1 Oct
Apartment in Annapolis
4.73 out of 5 average rating, 71 reviewsAmazing Views from Spa Creek 2BD Condo with Pool
24–31 Mar
Apartment in Betterton
4.93 out of 5 average rating, 30 reviews3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!
24 Jun – 1 Jul
Apartment in Rock Hall
5.0 out of 5 average rating, 10 reviewsWaterman's Delight ~ Best Harbor View Sunsets!
11–18 Aug
Apartment in Baltimore
5.0 out of 5 average rating, 32 reviewsHarbor Gem
19–26 Aug
Apartment in Annapolis
4.96 out of 5 average rating, 214 reviewsAnnapolis Waterfront Condo - Unit #: A-203
20–27 Aug
Quick stats about waterfront rentals in Annapolis
Total rentals
30 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
2.1K reviews
Nightly prices starting at
£96 before taxes and fees
Destinations to explore
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