House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Annapolis house rentals
House rentals with free parking
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Apr 3 – 10
Home in Glen Burnie
4.95 out of 5 average rating, 124 reviewsCozy Home with Relaxing Views - 10 mins. to BWI
Sep 21 – 28
Home in Crownsville
4.94 out of 5 average rating, 148 reviewsSevern River Waterfront Home
Aug 24 – 31
Home in Annapolis
4.89 out of 5 average rating, 182 reviewsCountry House on the Bay
Jan 20 – 27
Home in Edgewater
4.95 out of 5 average rating, 119 reviewsHouse in Edgewater Maryland
Jan 31 – Feb 7
Home in Annapolis
4.85 out of 5 average rating, 206 reviewsSpacious Home in Private Neighborhood with Beach
Feb 15 – 22
Home in Edgewater
4.95 out of 5 average rating, 38 reviewsRelaxing Turkey Point Retreat-Steps to the marina!
Feb 5 – 12
Home in Annapolis
4.95 out of 5 average rating, 41 reviewsNaptown Suite
Jan 3 – 10
House rentals with a pool
Home in Kent Narrows
5.0 out of 5 average rating, 278 reviewsChester Riverfront At Kent Narrows
Oct 19 – 26
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
Dec 11 – 18
Home in New Market
4.94 out of 5 average rating, 115 reviewsHistoric Peace and Plenty Farm: Pool House
Oct 20 – 27
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
Jul 7 – 14
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 15 – 22
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Mar 28 – Apr 4
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
Jan 8 – 15
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Apr 4 – 11
House rentals with a hot tub
Home in Grasonville
4.94 out of 5 average rating, 225 reviewsRiver Front, Private Single Family Home
Nov 3 – 10
Home in Deale
4.98 out of 5 average rating, 113 reviewsChesapeake Waterfront-Hot Tub-Kayaks-King Bed
Dec 11 – 18
Home in Silver Spring
5.0 out of 5 average rating, 118 reviewsRare New Build Home w/Hot Tub, Fire pit, Game Room
Dec 25 – Jan 1
Home in Edgewater
4.75 out of 5 average rating, 269 reviewsEdgewater/Mayo Getaway!
Aug 13 – 20
Home in Cambridge
4.95 out of 5 average rating, 100 reviewsPeaceful Historic House Near Water, with Hot Tub!
Jun 21 – 28
Home in Chestertown
5.0 out of 5 average rating, 104 reviewsWaterfront w/Pier &Walking Distance to Chestertown
Nov 9 – 16
Home in Arlington
4.86 out of 5 average rating, 264 reviewsArlington farmhouse w/easy access to everything DC
Oct 29 – Nov 5
Home in Arlington
4.92 out of 5 average rating, 130 reviewsLA Inspired Glasshouse Ping Pong 4min DC
Sep 14 – 21
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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