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 Hamilton
4.94 out of 5 average rating, 309 reviews*Cottage @ Firefly Cellars* VA Wine Country escape
Dec 17 – 24
Cottage in Reedville
4.9 out of 5 average rating, 161 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Nov 2 – 9
Cottage in Reedville
4.91 out of 5 average rating, 143 reviews"Dragonfly" Waterfront Cottage on Chesapeake Bay
Sep 12 – 19
Cottage in Heathsville
4.9 out of 5 average rating, 71 reviewsWaterfront Cottage w Private Beach & Hot Tub
Mar 23 – 30
Cottage in Saint Leonard
4.98 out of 5 average rating, 92 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
Jun 27 – Jul 4
Cottage in Montross
4.93 out of 5 average rating, 57 reviewsLakefront/Dock, Cove, Boats, HotTub, Woods & Beach
Jul 11 – 18
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Oct 6 – 13
Cottage in Annapolis
4.84 out of 5 average rating, 50 reviewsWaterfront cottage w/hot tub/ gated/ pier/ firepit
Sep 15 – 22
Pet-friendly cottage rentals
Cottage in Fredericksburg
4.79 out of 5 average rating, 441 reviews1840's Cottage: 3 miles from I-95/ Near Shopping
Mar 16 – 23
Cottage in Colonial Beach
4.91 out of 5 average rating, 116 reviewsShore Cottage Getaway - Water access
Jul 20 – 27
Cottage in Colonial Beach
4.95 out of 5 average rating, 153 reviewsBayside Cottage- In the Town with views
May 31 – Jun 7
Cottage in Annapolis
4.94 out of 5 average rating, 314 reviewsWright’s Cottage, Pets Welcome!
Jul 29 – Aug 5
Cottage in Leesburg
4.91 out of 5 average rating, 289 reviewsThe Cottage at Forest Hills Farm
Nov 26 – Dec 3
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 Annapolis
4.96 out of 5 average rating, 336 reviewsRelaxing Water Views - Mill Creek Cottage
Feb 22 – Mar 1
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Oct 4 – 11
Private cottage rentals
Cottage in Tracys Landing
4.9 out of 5 average rating, 337 reviewsCharming Waterfront on Chesapeake Bay
Jan 8 – 15
Cottage in Cambridge
4.98 out of 5 average rating, 108 reviewsChurch Creek - waterfront cottage & pool - private
Jan 31 – Feb 7
Cottage in Edgewater
4.99 out of 5 average rating, 129 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Dec 20 – 27
Cottage in Broomes Island
4.9 out of 5 average rating, 122 reviewsGorgeous Waterfront Home!
Apr 14 – 21
Cottage in Colonial Beach
4.83 out of 5 average rating, 142 reviewsSUPERB BEACH COTTAGE- Waterview, firepit, porch!
May 14 – 21
Cottage in North Beach
4.97 out of 5 average rating, 100 reviewsBell Estates-Brand New Bay View, Beautiful Cottage
Jan 1 – 8
Cottage in Saint Michaels
4.98 out of 5 average rating, 426 reviewsSt. Michaels-Historic Dist. Margaret Wells House
Mar 16 – 23
Cottage in Hague
5.0 out of 5 average rating, 81 reviewsPotomac River cheerful cottage
Dec 4 – 11
Destinations to explore
- Baltimore Vacation rentals
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- Cottage rentals Maryland
- Cottage rentals Maryland
- Rentals with an EV charger Southern Maryland
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