Cottage vacation rentals in Southern Maryland
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Southern Maryland
Guests agree: these cottages 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 cottage rentals
Cottage rentals with a hot tub
Cottage in Reedville
4.9 out of 5 average rating, 166 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Cottage in Reedville
4.91 out of 5 average rating, 149 reviews"Dragonfly" Waterfront Cottage on Chesapeake Bay
Cottage in Heathsville
4.9 out of 5 average rating, 77 reviewsWaterfront Cottage w Hot Tub, Kayaks, Fishing
Cottage in Montross
4.92 out of 5 average rating, 61 reviewsLakefront/Dock, Cove, Boats, HotTub, Woods & Beach
Cottage in Easton
5.0 out of 5 average rating, 84 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Cottage in Annapolis
4.85 out of 5 average rating, 54 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
Cottage in Lusby
New place to stayBayHollow: HOT TUB with treetop views
Cottage in Chesapeake Beach
4.5 out of 5 average rating, 18 reviewsAdorable Beach Cottage w/ Hot Tub & Tropical Bar!
Pet-friendly cottage rentals
Cottage in Deal Island
4.93 out of 5 average rating, 123 reviewsWater View Cottage
Cottage in Fredericksburg
4.79 out of 5 average rating, 449 reviews1840's Cottage: 3 miles from I-95/ Near Shopping
Cottage in Fredericksburg
4.84 out of 5 average rating, 361 reviewsRappahannock River Cottage, Near I-95! Sleeps 6!
Cottage in Colonial Beach
4.93 out of 5 average rating, 159 reviewsBayside Cottage- In the Town with views
Cottage in Saint Michaels
4.98 out of 5 average rating, 186 reviewsThe Little Anchor Cottage, St. Michaels, MD
Cottage in Annapolis
4.95 out of 5 average rating, 345 reviewsRelaxing Water Views - Mill Creek Cottage
Cottage in North Beach
4.94 out of 5 average rating, 131 reviewsClub Carp North Beach - Steps to the Bay!
Cottage in Neavitt
4.88 out of 5 average rating, 125 reviewsThe Middle Point Cottage at Saint Michaels
Private cottage rentals
Cottage in Tracys Landing
4.89 out of 5 average rating, 342 reviewsCharming Waterfront on Chesapeake Bay
Cottage in Colonial Beach
4.84 out of 5 average rating, 146 reviewsSUPERB BEACH COTTAGE- Waterview, firepit, porch!
Cottage in Reedville
4.95 out of 5 average rating, 118 reviewsBull Neck Cottage
Cottage in Cambridge
4.98 out of 5 average rating, 114 reviewsChurch Creek - waterfront cottage & pool - private
Cottage in Edgewater
4.99 out of 5 average rating, 133 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Cottage in Saint Michaels
4.98 out of 5 average rating, 437 reviewsSt. Michaels-Historic Dist. Margaret Wells House
Cottage in Reedville
4.9 out of 5 average rating, 175 reviewsChesapeake Bay Beach Cottage
Cottage in Kinsale
4.93 out of 5 average rating, 90 reviewsPeaceful Waterfront 3 BR/2BA
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