Waterfront holiday rentals in Annapolis
Find and book unique waterfront rentals on Airbnb
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, 174 reviewsHalcyon house. Lovely views on MD eastern shore.
30 Oct – 6 Nov
Flat in Essex
4.97 out of 5 average rating, 223 reviewsA place unique on sue creek
23–30 Jun
Flat in Chester
4.97 out of 5 average rating, 234 reviewsCozy Waterfront Apartment Chester, MD
24–31 Dec
Flat in Occoquan
4.89 out of 5 average rating, 416 reviewsAnne’s River View, couples, Historic Occoquan,hike
15–22 Oct
Flat in Deale
4.91 out of 5 average rating, 614 reviewsRomantic Wtrfrnt Flat+Solarium@Chesapeake Paradise
8–15 May
Flat in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
6–13 Feb
Flat in Alexandria
4.87 out of 5 average rating, 245 reviewsThe Duke Suite at Prince Street Inn
15–22 Jun
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
Waterfront house rentals
Home in Annapolis
4.98 out of 5 average rating, 156 reviewsQuiet Waterfront
23–30 Sep
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 apartment rentals
Apartment in Baltimore
4.9 out of 5 average rating, 174 reviewsHistoric Federal hills urban lifestyle
23–30 Jul
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, 6 reviewsCharming Annapolis Waterfront Condo
30 Nov – 7 Dec
Apartment in Rock Hall
5.0 out of 5 average rating, 10 reviewsWaterman's Delight ~ Best Harbor View Sunsets!
25 Jul – 1 Aug
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 Annapolis
4.73 out of 5 average rating, 71 reviewsAmazing Views from Spa Creek 2BD Condo with Pool
23–30 Mar
Apartment in Baltimore
5.0 out of 5 average rating, 32 reviewsHarbor Gem
17–24 Sep
Apartment in Annapolis
4.96 out of 5 average rating, 213 reviewsAnnapolis Waterfront Condo - Unit #: A-203
28 Aug – 4 Sep
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
€ 112 before taxes and fees
Destinations to explore
- Baltimore Holiday rentals
- Ocean City Holiday rentals
- Cape May Holiday rentals
- Wildwood Holiday rentals
- Rehoboth Beach Holiday rentals
- Arlington Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Waterfront rentals United States
- Waterfront rentals Washington
- Waterfront rentals Philadelphia
- Waterfront rentals Baltimore
- Family-friendly rentals Annapolis
- Rentals with a hot tub Annapolis
- Fitness-friendly rentals Annapolis
- Rentals with a patio Annapolis
- Rentals with lake access Annapolis
- Rentals with outdoor seating Annapolis
- Private suite rentals Annapolis
- Flat rentals Annapolis
- Apartment rentals Annapolis
- Rentals with pools Annapolis
- Rentals with a washing machine and dryer Annapolis
- Rentals with an EV charger Annapolis
- Townhouse rentals Annapolis
- Pet-friendly rentals Annapolis
- Rentals with breakfast Annapolis
- House rentals Annapolis
- Family-friendly rentals Annapolis
- Monthly Rentals Annapolis
- Rentals with a firepit Annapolis
- Rentals with a fireplace Annapolis
- Rentals with beach access Annapolis
- Waterfront rentals Maryland
- Waterfront rentals Anne Arundel County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom