House vacation rentals in Southern Maryland
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Top-rated house rentals in Southern Maryland
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 Southern Maryland house rentals
House rentals with a pool
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
Dec 11 – 18
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
Jul 9 – 16
Home in Montross
4.93 out of 5 average rating, 166 reviewsThe Glebe
Dec 4 – 11
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Sep 22 – 29
Home in Fairfax
4.96 out of 5 average rating, 145 reviews6BR Modern Home w/HEATED Pool & Screened in Porch
Jan 7 – 14
Home in Harwood
4.94 out of 5 average rating, 117 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
Jun 12 – 19
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 17 – 24
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Sep 22 – 29
Weekly house rentals
Home in Newburg
4.92 out of 5 average rating, 104 reviewsThe River House, a Wicomico Beach Retreat
Jan 4 – 11
Home in Lusby
5.0 out of 5 average rating, 135 reviewsCove Point Beach Home 1 &1/2 blocks to Beach
Oct 14 – 21
Home in Hague
5.0 out of 5 average rating, 4 reviewsSeahorse Inn
Jul 17 – 24
Home in Lusby
4.92 out of 5 average rating, 37 reviewsSoul Oasis - home on the Chesapeake Bay
Dec 6 – 13
Home in Leonardtown
4.95 out of 5 average rating, 43 reviewsOld Bay Inn
Sep 11 – 18
Home in Colonial Beach
4.97 out of 5 average rating, 39 reviewsWaterfront Paradise with own Beach, Kayak, & Grill
Dec 12 – 19
Home in Piney Point
4.92 out of 5 average rating, 12 reviews2 Bedroom Cozy Beach Cottage
Sep 6 – 13
Home in Colonial Beach
4.98 out of 5 average rating, 65 reviewsMarji's Postcard Inn - waterview
May 13 – 20
Private house rentals
Home in Solomons
5.0 out of 5 average rating, 41 reviewsThe Little House on Back Creek
Mar 31 – Apr 7
Home in Leonardtown
5.0 out of 5 average rating, 15 reviewsWaterfront Cottage w/ Incredible Views
Jul 7 – 14
Home in Huntingtown
5.0 out of 5 average rating, 19 reviewsHouse near Patuxent River
May 31 – Jun 7
Home in Saint Leonard
4.97 out of 5 average rating, 38 reviewsBlue Pearl-Luxury estate with private dock/jacuzzi
Nov 15 – 22
Home in Solomons
5.0 out of 5 average rating, 30 reviewsBlue Heron Retreat on the Water
May 2 – 9
Home in Woodbridge
4.98 out of 5 average rating, 61 reviewsSpacious basement apartment with private entrance
Sep 28 – Oct 5
Home in Colonial Beach
4.97 out of 5 average rating, 29 reviewsRiver Refresh - Waterfront with Spa on Placid Bay
Jan 23 – 30
Home in Mechanicsville
4.97 out of 5 average rating, 59 reviewsStylish waterfront retreat, 1 hr to DC Summer fun
Apr 11 – 18
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