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, 119 reviewsHouse in Edgewater Maryland
1–8 Feb
Home in Kent Narrows
5.0 out of 5 average rating, 278 reviewsChester Riverfront At Kent Narrows
16–23 Oct
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
3–10 Sep
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
24 Apr – 1 May
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
27 Jan – 3 Feb
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
15–22 Nov
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
28 Oct – 4 Nov
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
19–26 Jun
Weekly house rentals
Home in Edgewater
4.98 out of 5 average rating, 100 reviewsLuxury Modern Home on Water+Hotub- Annapolis 25min
17–24 Jun
Home in Annapolis
4.85 out of 5 average rating, 196 reviewsHistoric Home Steps from City Center & Waterfront
9–16 Feb
Home in Glen Burnie
4.95 out of 5 average rating, 124 reviewsCozy Home with Relaxing Views - 10 mins. to BWI
21–28 Sep
Home in Annapolis
4.89 out of 5 average rating, 182 reviewsCountry House on the Bay
28 Sep – 5 Oct
Home in Crownsville
4.94 out of 5 average rating, 148 reviewsSevern River Waterfront Home
24–31 Aug
Home in Crownsville
5.0 out of 5 average rating, 58 reviews"Hilltop Hideaway"- Private basement suite
8–15 Sep
Home in Arnold
4.94 out of 5 average rating, 48 reviewsBring A Boat! Waterfront home-w/basement apt+dock!
1–8 Nov
Home in Annapolis
4.89 out of 5 average rating, 27 reviewsCute cozy rancher close to down town Annapolis
26 Nov – 3 Dec
Private house rentals
Home in Severn
4.95 out of 5 average rating, 20 reviewsHidden Haven Roost
27 Nov – 4 Dec
Home in Annapolis
5.0 out of 5 average rating, 40 reviewsElegant & Authentic Annapolis
19–26 May
Home in Edgewater
4.95 out of 5 average rating, 38 reviewsRelaxing Turkey Point Retreat-Steps to the marina!
9–16 Dec
Home in Annapolis
4.97 out of 5 average rating, 34 reviewsCharming Annapolis Retreat with Hidden Wine Room
14–21 Nov
Home in Annapolis
4.99 out of 5 average rating, 83 reviewsCharming Downtwn Home, Private Parking Patio&Yard!
23–30 Mar
Home in Annapolis
4.99 out of 5 average rating, 84 reviewsBoutique Historic Home Steps from the State House!
15–22 Dec
Home in Shady Side
4.97 out of 5 average rating, 65 reviewsCanary Pointe-A popular getaway for 2!
8–15 Jul
Home in Riviera Beach
5.0 out of 5 average rating, 21 reviewsCheerful 2 Home
17–24 Oct
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
12T reviews
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