Waterfront holiday rentals in Annapolis
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Top-rated waterfront accommodation in Annapolis
Guests agree: These waterfront accommodation options 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 Annapolis waterfront rentals
Waterfront apartment accommodation
Apartment in Grasonville
4.89 out of 5 average rating, 174 reviewsHalcyon house. Lovely views on MD eastern shore.
30 Oct – 6 Nov
Apartment in Essex
4.97 out of 5 average rating, 223 reviewsA place unique on sue creek
23 – 30 June
Apartment in Chester
4.97 out of 5 average rating, 234 reviewsCozy Waterfront Apartment Chester, MD
24 – 31 Dec
Apartment in Occoquan
4.89 out of 5 average rating, 416 reviewsAnne’s River View, couples, Historic Occoquan,hike
15 – 22 Oct
Apartment in Deale
4.91 out of 5 average rating, 614 reviewsRomantic Wtrfrnt Flat+Solarium@Chesapeake Paradise
8 – 15 May
Apartment in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
6 – 13 Feb
Apartment in Alexandria
4.87 out of 5 average rating, 245 reviewsThe Duke Suite at Prince Street Inn
15 – 22 June
Apartment in Washington
4.8 out of 5 average rating, 384 reviewsCozy & modern apt in the heart of town King Bed
30 May – 6 June
Waterfront house rentals
Home in Annapolis
4.98 out of 5 average rating, 156 reviewsQuiet Waterfront
23 – 30 Sept
Home in Edgewater
4.98 out of 5 average rating, 100 reviewsLuxury Modern Home on Water+Hotub- Annapolis 25min
3 – 10 Oct
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
8 – 15 Mar
Home in Annapolis
4.89 out of 5 average rating, 182 reviewsCountry House on the Bay
20 – 27 Jan
Home in Crownsville
4.94 out of 5 average rating, 148 reviewsSevern River Waterfront Home
24 – 31 Aug
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
10 – 17 Dec
Home in Grasonville
4.94 out of 5 average rating, 225 reviewsRiver Front, Private Single Family Home
3 – 10 Nov
Home in Kent Narrows
5.0 out of 5 average rating, 278 reviewsChester Riverfront At Kent Narrows
19 – 26 Oct
Waterfront condo accommodation
Condo in Baltimore
4.9 out of 5 average rating, 174 reviewsHistoric Federal hills urban lifestyle
23 – 30 July
Condo in Washington
4.83 out of 5 average rating, 18 reviewsHistorical Georgetown Modern Penthouse 12 min DCA
27 May – 3 June
Condo in Annapolis
5.0 out of 5 average rating, 6 reviewsCharming Annapolis Waterfront Condo
30 Nov – 7 Dec
Condo in Rock Hall
5.0 out of 5 average rating, 10 reviewsWaterman's Delight ~ Best Harbor View Sunsets!
25 July – 1 Aug
Condo in Betterton
4.93 out of 5 average rating, 30 reviews3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!
24 June – 1 July
Condo in Annapolis
4.73 out of 5 average rating, 71 reviewsAmazing Views from Spa Creek 2BD Condo with Pool
23 – 30 Mar
Condo in Baltimore
5.0 out of 5 average rating, 32 reviewsHarbor Gem
17 – 24 Sept
Condo in Annapolis
4.96 out of 5 average rating, 213 reviewsAnnapolis Waterfront Condo - Unit #: A-203
28 Aug – 4 Sept
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
$184 AUD before taxes and fees
Destinations to explore
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