Beachfront holiday rentals in Southern Maryland
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Southern Maryland
Guests agree: these beachfront homes 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 beachfront rentals in Southern Maryland
Pet-friendly beachfront home rentals
Home in Lusby
4.99 out of 5 average rating, 114 reviewsCoastal Oasis On The Chesapeake, King Bd sleeps 12
18–25 Sep
Home in Lusby
4.94 out of 5 average rating, 157 reviewsWaterfront Home on the Chesapeake Bay-Pvt Beach
18–25 Apr
Home in Newburg
4.92 out of 5 average rating, 104 reviewsThe River House, a Wicomico Beach Retreat
4–11 Dec
Home in Shady Side
5.0 out of 5 average rating, 119 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
4–11 Mar
Home in Colonial Beach
4.93 out of 5 average rating, 115 reviews‘Pipe Dream’ - 3BD/2.5BTH - Awesome water view!
27 Sep – 4 Oct
Cottage in Reedville
4.9 out of 5 average rating, 162 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
2–9 Apr
Cottage in Colonial Beach
4.94 out of 5 average rating, 154 reviewsBayside Cottage- In the Town with views
12–19 Jul
Home in Solomons
4.89 out of 5 average rating, 125 reviewsPerfect spot for a Vacay!
11–18 Jul
Beachfront home rentals with a pool
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
19–26 Jan
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
17–24 Feb
Villa in Montross
4.83 out of 5 average rating, 76 reviewsBeach Retreat
13–20 Feb
Home in Montross
5.0 out of 5 average rating, 49 reviewsWaterfront+Kayaks+Gameroom+Pool+Firepit+EV/Dog OK
23–30 Sep
Cottage in Heathsville
4.83 out of 5 average rating, 59 reviewsRiverfront Retreat with PRIVATE POOL and BEACH!!
3–10 Oct
Apartment in Colonial Beach
5.0 out of 5 average rating, 24 reviewsRooftop bay and river views
29 Nov – 6 Dec
Guest house in Colonial Beach
4.96 out of 5 average rating, 48 reviewsBeach Carriage House with Pool and Cabana
13–20 Sep
Guest house in Queenstown
4.9 out of 5 average rating, 21 reviewsWaterfront Getaway
24 Apr – 1 May
Private beachfront home rentals
Home in Lexington Park
4.96 out of 5 average rating, 140 reviewsPrivate beach retreat in historic St. Mary's City
20–27 Sep
Cottage in North Beach
4.96 out of 5 average rating, 274 reviewsWaterfront Cottage Near Herrington and North Beach
26 Jul – 2 Aug
Home in Colonial Beach
4.84 out of 5 average rating, 128 reviews*WATERFRONT BEACH HOUSE PARADISE*
29 Sep – 6 Oct
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
12–19 Jan
Cabin in Lusby
4.85 out of 5 average rating, 132 reviews2-bedroom lake-house with a magnificent view
25 Oct – 1 Nov
Home in Hague
4.97 out of 5 average rating, 146 reviewsOsprey's roost: Summer 2023
5–12 Oct
Cabin in Reedville
4.97 out of 5 average rating, 190 reviewsDinna Fash-3 BR Waterfront Log Cabin
15–22 Nov
Home in St. Leonard
4.91 out of 5 average rating, 162 reviewsCozy Cottage on the Chesapeake Bay
27 Oct – 3 Nov
Destinations to explore
- Baltimore Holiday rentals
- Ocean City Holiday rentals
- Richmond Holiday rentals
- Rehoboth Beach Holiday rentals
- Arlington Holiday rentals
- Charlottesville Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Beachfront rentals Maryland
- Beachfront rentals Maryland
- Smoking-friendly rentals Southern Maryland
- Apartment rentals Southern Maryland
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- Rentals with outdoor seating Southern Maryland
- Rentals with lake access Southern Maryland
- Rentals with a hot tub Southern Maryland
- Pet-friendly rentals Southern Maryland
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- Guest house rentals Southern Maryland
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- Waterfront rentals Southern Maryland
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- Monthly Rentals Southern Maryland
- Rentals with beach access Southern Maryland
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- Rentals with an EV charger Southern Maryland
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- Rentals with a kayak Southern Maryland
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