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
Get the amount of space that is right for you
Popular amenities for house rentals in Annapolis
House rentals with a pool
Home in Edgewater
4.95 out of 5 average rating, 123 reviewsHouse in Edgewater Maryland
Home in Tracys Landing
4.99 out of 5 average rating, 172 reviewsThe Little Gypsy BoHome
Home in Kent Narrows
5 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 Severn
4.81 out of 5 average rating, 107 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Home in Chesapeake Beach
4.91 out of 5 average rating, 113 reviewsIndoor pool/spa nestled in Southern Md. woods.
Weekly house rentals
Home in Crownsville
4.94 out of 5 average rating, 148 reviewsSevern River Waterfront Home
Home in Annapolis
4.98 out of 5 average rating, 160 reviewsQuiet Waterfront
Home in Annapolis
4.99 out of 5 average rating, 175 reviews3BR/2BA Annapolis Cottage
Home in Silver Spring
4.99 out of 5 average rating, 160 reviewsEntire Guest Suite/Apt in Silver Spring/FDA
Home in Arnold
4.94 out of 5 average rating, 18 reviewsPrivate Arnold basement apt- Close to The Point!
Home in Annapolis
4.89 out of 5 average rating, 53 reviewsAdorable 1 bedroom apartment in downtown Annapolis
Home in Annapolis
4.9 out of 5 average rating, 77 reviews2 blocks to Main st. Walk-up Rowhouse, Value Stay
Home in Edgewater
4.96 out of 5 average rating, 46 reviewsRelaxing Turkey Point Retreat-Steps to the marina!
Private house rentals
Home in Shady Side
4.97 out of 5 average rating, 76 reviewsCanary Pointe-A popular getaway for 2!
Home in Harwood
4.97 out of 5 average rating, 33 reviewsQuiet Farm Stay near Annapolis
Home in Annapolis
4.96 out of 5 average rating, 80 reviewsGreen On Fleet - Rowhouse in Historic Annapolis
Home in Annapolis
4.98 out of 5 average rating, 40 reviewsCharming Annapolis Retreat with Hidden Wine Room
Home in Annapolis
5 out of 5 average rating, 96 reviewsHistoric & sunny home steps from USNA/downtown
Home in Annapolis
4.99 out of 5 average rating, 86 reviewsBoutique Historic Home Steps from the State House!
Home in Pasadena
5 out of 5 average rating, 21 reviewsWaterfront CHeerful 2 with Private home
Home in Stevensville
5 out of 5 average rating, 24 reviewsAway at the Bay: New Home on the Chesapeake Bay!
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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