Cottage vacation rentals in Southern Maryland
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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
4.91 out of 5 average rating, 143 reviews"Dragonfly" Waterfront Cottage on Chesapeake Bay
Sep 28 – Oct 5
Cottage in Reedville
4.9 out of 5 average rating, 162 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Feb 15 – 22
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Jan 30 – Feb 6
Cottage in Saint Leonard
4.98 out of 5 average rating, 92 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
Apr 18 – 25
Cottage in Heathsville
4.9 out of 5 average rating, 71 reviewsWaterfront Cottage w Private Beach & Hot Tub
Dec 22 – 29
Cottage in Montross
4.91 out of 5 average rating, 58 reviewsLakefront/Dock, Cove, Boats, HotTub, Woods & Beach
Mar 18 – 25
Cottage in Heathsville
4.89 out of 5 average rating, 18 reviewsWaterfront Heathsville Cottage w/ Dock & Hot Tub!
Mar 7 – 14
Cottage in Chesapeake Beach
4.5 out of 5 average rating, 18 reviewsAdorable Beach Cottage w/ Hot Tub & Tropical Bar!
Feb 23 – Mar 2
Pet-friendly cottage rentals
Cottage in Colonial Beach
4.95 out of 5 average rating, 153 reviewsBayside Cottage- In the Town with views
Jul 12 – 19
Cottage in North Beach
4.95 out of 5 average rating, 125 reviewsClub Carp North Beach - Steps to the Bay!
Aug 30 – Sep 6
Cottage in Saint Michaels
4.98 out of 5 average rating, 176 reviewsThe Little Anchor Cottage, St. Michaels, MD
Apr 4 – 11
Cottage in Fredericksburg
4.84 out of 5 average rating, 354 reviewsRappahannock River Cottage, Near I-95! Sleeps 6!
Mar 21 – 28
Cottage in North Beach
4.97 out of 5 average rating, 101 reviewsBell Estates-Brand New Bay View, Beautiful Cottage
Jan 9 – 16
Cottage in Neavitt
4.9 out of 5 average rating, 124 reviewsThe Middle Point Cottage at Saint Michaels
Apr 18 – 25
Cottage in Tall Timbers
4.9 out of 5 average rating, 106 reviewsSunsets on Potomac, Woodland Cottage with Views
Sep 13 – 20
Cottage in Deale
4.81 out of 5 average rating, 167 reviewsWatrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Sep 5 – 12
Private cottage rentals
Cottage in Tracys Landing
4.9 out of 5 average rating, 338 reviewsCharming Waterfront on Chesapeake Bay
Sep 12 – 19
Cottage in Edgewater
4.99 out of 5 average rating, 129 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Sep 27 – Oct 4
Cottage in Cambridge
4.98 out of 5 average rating, 108 reviewsChurch Creek - waterfront cottage & pool - private
Apr 21 – 28
Cottage in Saint Michaels
4.98 out of 5 average rating, 426 reviewsSt. Michaels-Historic Dist. Margaret Wells House
Mar 31 – Apr 7
Cottage in Broomes Island
4.9 out of 5 average rating, 122 reviewsGorgeous Waterfront Home!
May 10 – 17
Cottage in Colonial Beach
4.83 out of 5 average rating, 142 reviewsSUPERB BEACH COTTAGE- Waterview, firepit, porch!
May 14 – 21
Cottage in Reedville
4.9 out of 5 average rating, 173 reviewsChesapeake Bay Beach Cottage
Oct 21 – 28
Cottage in Stevensville
4.94 out of 5 average rating, 132 reviewsCottage on the Bay - Kent Island
Oct 3 – 10
Destinations to explore
- Baltimore Vacation rentals
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- Cottage rentals Maryland
- Cottage rentals Maryland
- Rentals with a kayak Southern Maryland
- Waterfront rentals Southern Maryland
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- Condo rentals Southern Maryland
- Rentals with a patio Southern Maryland
- Rentals with pools Southern Maryland
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- Rentals with lake access Southern Maryland
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