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 Annapolis house rentals
House rentals with a pool
Home in Edgewater
4.95 out of 5 average rating, 119 reviewsHouse in Edgewater Maryland
3–10 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!
26 Feb – 5 Mar
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
12–19 Dec
Home in Harwood
4.94 out of 5 average rating, 117 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
15–22 Jun
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
29 Jan – 5 Feb
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
18–25 Nov
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
5–12 Feb
Weekly house rentals
Home in Annapolis
4.85 out of 5 average rating, 196 reviewsHistoric Home Steps from City Center & Waterfront
22–29 Mar
Home in Glen Burnie
4.95 out of 5 average rating, 124 reviewsCozy Home with Relaxing Views - 10 mins. to BWI
19–26 Sep
Home in Annapolis
4.89 out of 5 average rating, 182 reviewsCountry House on the Bay
6–13 Nov
Home in Crownsville
5.0 out of 5 average rating, 58 reviews"Hilltop Hideaway"- Private basement suite
19–26 Sep
Home in Annapolis
4.89 out of 5 average rating, 27 reviewsCute cozy rancher close to down town Annapolis
17–24 Jan
Home in Arnold
4.94 out of 5 average rating, 48 reviewsBring A Boat! Waterfront home-w/basement apt+dock!
23–30 Jan
Home in Annapolis
5.0 out of 5 average rating, 40 reviewsElegant & Authentic Annapolis
15–22 Oct
Home in Annapolis
4.88 out of 5 average rating, 48 reviewsAdorable 1 bedroom apartment in downtown Annapolis
15–22 Jul
Private house rentals
Home in Annapolis
4.97 out of 5 average rating, 34 reviewsCharming Annapolis Retreat with Hidden Wine Room
2–9 Nov
Home in Annapolis
5.0 out of 5 average rating, 86 reviewsHistoric & sunny home steps from USNA/downtown
9–16 Sep
Home in Annapolis
4.99 out of 5 average rating, 83 reviewsCharming Downtwn Home, Private Parking Patio&Yard!
13–20 Aug
Home in Riviera Beach
5.0 out of 5 average rating, 21 reviewsCheerful 2 Home
13–20 Aug
Home in Arnold
4.94 out of 5 average rating, 17 reviewsPrivate Arnold basement apt- Close to The Point!
8–15 Jan
Home in Shady Side
4.97 out of 5 average rating, 66 reviewsCanary Pointe-A popular getaway for 2!
12–19 Apr
Home in Annapolis
4.99 out of 5 average rating, 84 reviewsBoutique Historic Home Steps from the State House!
20–27 Dec
Home in Annapolis
4.97 out of 5 average rating, 67 reviewshot tub, pet friendly, fenced yard in Annapolis
17–24 Apr
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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