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
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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.
31 Oct – 7 Nov
Flat in Essex
4.97 out of 5 average rating, 223 reviewsA place unique on sue creek
12–19 Apr
Flat in Deale
4.91 out of 5 average rating, 614 reviewsRomantic Wtrfrnt Flat+Solarium@Chesapeake Paradise
8–15 Nov
Flat in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
20–27 Feb
Flat in Alexandria
4.87 out of 5 average rating, 245 reviewsThe Duke Suite at Prince Street Inn
6–13 Oct
Flat in Washington
4.8 out of 5 average rating, 384 reviewsCozy & modern apt in the heart of town King Bed
30 May – 6 Jun
Flat in Annapolis
4.98 out of 5 average rating, 90 reviewsOne bedroom apartment in Annapolis
10–17 Nov
Flat in Pasadena
5.0 out of 5 average rating, 6 reviewsRelaxing Waterfront Apartment!
19–26 Aug
Waterfront house rentals
Home in Annapolis
4.98 out of 5 average rating, 156 reviewsQuiet Waterfront
23–30 Sep
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
3–10 Sep
Home in Edgewater
4.98 out of 5 average rating, 100 reviewsLuxury Modern Home on Water+Hotub- Annapolis 25min
17–24 Jun
Home in Annapolis
4.89 out of 5 average rating, 182 reviewsCountry House on the Bay
28 Sep – 5 Oct
Home in Crownsville
4.94 out of 5 average rating, 148 reviewsSevern River Waterfront Home
24–31 Aug
Home in Grasonville
4.94 out of 5 average rating, 226 reviewsRiver Front, Private Single Family Home
17–24 Nov
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
24 Apr – 1 May
Home in Kent Narrows
5.0 out of 5 average rating, 278 reviewsChester Riverfront At Kent Narrows
16–23 Oct
Waterfront apartment rentals
Apartment in Baltimore
4.9 out of 5 average rating, 175 reviewsHistoric Federal hills urban lifestyle
28 Nov – 5 Dec
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
12–19 Dec
Apartment in Rock Hall
5.0 out of 5 average rating, 10 reviewsWaterman's Delight ~ Best Harbor View Sunsets!
27 Jan – 3 Feb
Apartment in Betterton
4.93 out of 5 average rating, 30 reviews3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!
20–27 Sep
Apartment in Annapolis
4.73 out of 5 average rating, 71 reviewsAmazing Views from Spa Creek 2BD Condo with Pool
5–12 Jan
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, 213 reviewsAnnapolis Waterfront Condo - Unit #: A-203
24 Nov – 1 Dec
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
2.1T reviews
Nightly prices starting at
₹10,009 before taxes and fees
Destinations to explore
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