House holiday 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.
Holiday rentals for every style
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Popular amenities for house rentals in Southern Maryland
House rentals with a pool
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
27 Mar – 3 Apr
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
5–12 Feb
Home in Montross
4.93 out of 5 average rating, 167 reviewsThe Glebe
4–11 Dec
Home in Fairfax
4.96 out of 5 average rating, 146 reviews6BR Modern Home w/HEATED Pool & Screened in Porch
5–12 Jan
Home in Harwood
4.94 out of 5 average rating, 118 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
10–17 May
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
29 Jan – 5 Feb
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
16–23 Oct
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
20–27 Apr
Weekly house rentals
Home in Lexington Park
4.96 out of 5 average rating, 140 reviewsPrivate beach retreat in historic St. Mary's City
19–26 Sep
Home in Hague
4.8 out of 5 average rating, 5 reviewsSeahorse Inn
26 Apr – 3 May
Home in Colonial Beach
4.98 out of 5 average rating, 40 reviewsWaterfront Paradise with own Beach, Kayak, & Grill
13–20 Mar
Home in Lusby
4.92 out of 5 average rating, 39 reviewsSoul Oasis - home on the Chesapeake Bay
16–23 Sep
Home in Leonardtown
4.96 out of 5 average rating, 28 reviewsWater's Edge Cottage | Luxury Retreat
23–30 Sep
Home in Colonial Beach
4.98 out of 5 average rating, 66 reviewsMarji's Postcard Inn - waterview
13–20 May
Home in Montross
4.86 out of 5 average rating, 35 reviewsThe Haven at King Copsico - Comfortable and Cozy
8–15 Sep
Home in Colonial Beach
4.98 out of 5 average rating, 93 reviewsSunnyside Up - Dog Friendly Waterfront Cottage
18–25 Dec
Private house rentals
Home in Solomons
5.0 out of 5 average rating, 42 reviewsThe Little House on Back Creek
6–13 Mar
Home in Waldorf
5.0 out of 5 average rating, 64 reviewsSpacious Studio Apartment with private entrance
23–30 Aug
Home in Saint Leonard
4.98 out of 5 average rating, 40 reviewsBlue Pearl-Luxury estate with private dock/jacuzzi
15–22 Nov
Home in Hollywood
5.0 out of 5 average rating, 41 reviewsWaterfront Home: Osprey Getaway
16–23 Oct
Home in Newburg
4.92 out of 5 average rating, 49 reviewsPeaceful waterfront home, 1-hour from DC
4–11 Mar
Home in Huntingtown
5.0 out of 5 average rating, 20 reviewsHouse near Patuxent River
1–8 Jun
Home in Colonial Beach
4.97 out of 5 average rating, 30 reviewsRiver Refresh - Waterfront with Spa on Placid Bay
7–14 Dec
Home in Cobb Island
5.0 out of 5 average rating, 30 reviewsRiver Front 3 bedroom home with pier and beach.
28 Apr – 5 May
Destinations to explore
- Baltimore Holiday rentals
- Ocean City Holiday rentals
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- Rehoboth Beach Holiday rentals
- Arlington Holiday rentals
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- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
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