House holiday rentals in Annapolis
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Top-rated house rentals in Annapolis
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for house rentals in Annapolis
House rentals with a pool
Home in Tracys Landing
4.99 out of 5 average rating, 172 reviewsThe Little Gypsy BoHome
Home in Edgewater
4.95 out of 5 average rating, 123 reviewsHouse in Edgewater Maryland
Home in Kent Narrows
5.0 out of 5 average rating, 281 reviewsChester Riverfront At Kent Narrows
Home in Saint Michaels
4.97 out of 5 average rating, 240 reviewsMiles Aweigh
Home in Harwood
4.94 out of 5 average rating, 119 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
Home in Cambridge
4.96 out of 5 average rating, 102 reviewsWaterfront, Fabulous Home for Families with Pool!
Home in Chesapeake Beach
4.91 out of 5 average rating, 112 reviewsIndoor pool/spa nestled in Southern Md. woods.
Home in Severn
4.81 out of 5 average rating, 106 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Weekly house rentals
Home in Cambridge
4.92 out of 5 average rating, 186 reviewsGuest House: Farm homestead
Home in Annapolis
4.97 out of 5 average rating, 116 reviewsGorgeous Historic Downtown Annapolis House
Home in Annapolis
4.89 out of 5 average rating, 185 reviewsCountry House on the Bay
Home in Annapolis
4.92 out of 5 average rating, 105 reviewsEastport Haven House
Home in Glen Burnie
4.97 out of 5 average rating, 122 reviews12 M to Naval Acadmey | WATERFRONT|Calming Paradis
Home in Annapolis
4.99 out of 5 average rating, 175 reviews3BR/2BA Annapolis Cottage
Home in Glen Burnie
4.97 out of 5 average rating, 402 reviewsSecluded acre near BWI and Baltimore
Home in Annapolis
4.98 out of 5 average rating, 159 reviewsQuiet Waterfront
Private house rentals
Home in Arnold
4.94 out of 5 average rating, 17 reviewsPrivate Arnold basement apt- Close to The Point!
Home in Crownsville
5.0 out of 5 average rating, 64 reviews"Hilltop Hideaway"- Private basement suite
Home in Edgewater
4.96 out of 5 average rating, 45 reviewsRelaxing Turkey Point Retreat-Steps to the marina!
Home in Arnold
4.91 out of 5 average rating, 53 reviewsBring A Boat! Waterfront home-w/basement apt+dock!
Home in Harwood
4.97 out of 5 average rating, 32 reviewsQuiet Farm Stay near Annapolis
Home in Annapolis
4.96 out of 5 average rating, 55 reviewsAnnapolis Waterfront Home Private Fish/Crab Pier
Home in Annapolis
4.97 out of 5 average rating, 39 reviewsCharming Annapolis Retreat with Hidden Wine Room
Home in Annapolis
5.0 out of 5 average rating, 95 reviewsHistoric & sunny home steps from USNA/downtown
Quick stats about house rentals in Annapolis
Total rentals
390 properties
Rentals with dedicated workspaces
240 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
120 properties allow pets
Family-friendly rentals
330 properties are a good fit for families
Total number of reviews
12K reviews
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