House vacation rentals in Southern Maryland
Find and book unique houses on Airbnb
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 Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
Jul 15 – 22
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!
Dec 13 – 20
Home in Fairfax
4.96 out of 5 average rating, 146 reviews6BR Modern Home w/HEATED Pool & Screened in Porch
Mar 4 – 11
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Dec 8 – 15
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 24 – Dec 1
Home in Edgewater
4.95 out of 5 average rating, 120 reviewsHouse in Edgewater Maryland
Nov 4 – 11
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
Jan 3 – 10
Weekly house rentals
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Mar 21 – 28
Home in Lusby
4.99 out of 5 average rating, 114 reviewsCoastal Oasis On The Chesapeake, King Bd sleeps 12
Aug 16 – 23
Home in Lusby
4.99 out of 5 average rating, 176 reviewsCove Point Cottage with Chesapeake Bay views
Oct 20 – 27
Home in Leonardtown
4.95 out of 5 average rating, 43 reviewsOld Bay Inn
Jul 15 – 22
Home in Hague
4.8 out of 5 average rating, 5 reviewsSeahorse Inn
Apr 2 – 9
Home in Leonardtown
4.96 out of 5 average rating, 27 reviewsWater's Edge Cottage | Luxury Retreat
Jan 19 – 26
Home in Colonial Beach
4.98 out of 5 average rating, 40 reviewsWaterfront Paradise with own Beach, Kayak, & Grill
Feb 23 – Mar 2
Home in Lusby
4.92 out of 5 average rating, 38 reviewsSoul Oasis - home on the Chesapeake Bay
Sep 2 – 9
Private house rentals
Home in Solomons
5.0 out of 5 average rating, 42 reviewsThe Little House on Back Creek
Jan 22 – 29
Home in Leonardtown
5.0 out of 5 average rating, 16 reviewsWaterfront Cottage w/ Incredible Views
Jul 6 – 13
Home in Colonial Beach
4.98 out of 5 average rating, 65 reviewsMarji's Postcard Inn - waterview
Sep 27 – Oct 4
Home in Saint Leonard
4.97 out of 5 average rating, 39 reviewsBlue Pearl-Luxury estate with private dock/jacuzzi
Nov 15 – 22
Home in Hague
4.96 out of 5 average rating, 83 reviewsYear-Round River Escape with Indoor Pool & Beach
Dec 6 – 13
Home in Lusby
5.0 out of 5 average rating, 62 reviewsWaterfront with sweeping bay view & private beach
Dec 16 – 23
Home in Montross
4.86 out of 5 average rating, 35 reviewsThe Haven at King Copsico - Comfortable and Cozy
Sep 30 – Oct 7
Home in Colonial Beach
4.97 out of 5 average rating, 30 reviewsRiver Refresh - Waterfront with Spa on Placid Bay
Dec 16 – 23
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