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 a pool
Home in Edgewater
4.95 out of 5 average rating, 118 reviewsHouse in Edgewater Maryland
Jan. 31 – Feb. 7
Home in Kent Narrows
5.0 out of 5 average rating, 278 reviewsChester Riverfront At Kent Narrows
Oct. 19 – 26
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Apr. 3 – 10
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
Weekly house rentals
Home in Annapolis
4.85 out of 5 average rating, 196 reviewsHistoric Home Steps from City Center & Waterfront
Feb. 9 – 16
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, 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
Home in Annapolis
4.87 out of 5 average rating, 47 reviewsAdorable 1 bedroom apartment in downtown Annapolis
Feb. 21 – 28
Home in Arnold
4.94 out of 5 average rating, 48 reviewsBring A Boat! Waterfront home-w/basement apt+dock!
Dec. 2 – 9
Private house rentals
Home in Arnold
4.94 out of 5 average rating, 17 reviewsPrivate Arnold basement apt- Close to The Point!
Mar. 22 – 29
Home in Severna Park
4.92 out of 5 average rating, 24 reviewsSerene setting
Oct. 21 – 28
Home in Edgewater
4.97 out of 5 average rating, 30 reviewsEntire Beach House with Pool and Hot Tub
Oct. 31 – Nov. 7
Home in Annapolis
5.0 out of 5 average rating, 85 reviewsHistoric & sunny home steps from USNA/downtown
Jul. 7 – 14
Home in Severn
4.95 out of 5 average rating, 19 reviewsHidden Haven Roost
Aug. 26 – Sep. 2
Home in Annapolis
4.97 out of 5 average rating, 34 reviewsCharming Annapolis Retreat with Hidden Wine Room
Sep. 17 – 24
Home in Annapolis
4.99 out of 5 average rating, 83 reviewsCharming Downtwn Home, Private Parking Patio&Yard!
Sep. 27 – Oct. 4
Home in Riviera Beach
5.0 out of 5 average rating, 21 reviewsCheerful 2 Home
Mar. 17 – 24
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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