Cottage holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Southern Maryland
Cottage rentals with a hot tub
Cottage in Reedville
4.9 out of 5 average rating, 165 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Cottage in Reedville
4.91 out of 5 average rating, 147 reviews"Dragonfly" Waterfront Cottage on Chesapeake Bay
Cottage in Saint Leonard
4.98 out of 5 average rating, 96 reviewsHot Tub, Block to Beach, Fire Pit, Screened deck
Cottage in Heathsville
4.89 out of 5 average rating, 75 reviewsWaterfront Cottage w Private Beach & Hot Tub
Cottage in Easton
5.0 out of 5 average rating, 83 reviewsCottage on Solitude Creek, Hot Tub, Pool & Firepit
Cottage in Montross
4.92 out of 5 average rating, 59 reviewsLakefront/Dock, Cove, Boats, HotTub, Woods & Beach
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 Colonial Beach
4.94 out of 5 average rating, 156 reviewsBayside Cottage- In the Town with views
Cottage in Fredericksburg
4.79 out of 5 average rating, 446 reviews1840's Cottage: 3 miles from I-95/ Near Shopping
Cottage in Westover
4.92 out of 5 average rating, 145 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Cottage in Saint Michaels
4.98 out of 5 average rating, 183 reviewsThe Little Anchor Cottage, St. Michaels, MD
Cottage in Fredericksburg
4.84 out of 5 average rating, 360 reviewsRappahannock River Cottage, Near I-95! Sleeps 6!
Cottage in North Beach
4.94 out of 5 average rating, 128 reviewsClub Carp North Beach - Steps to the Bay!
Cottage in Neavitt
4.9 out of 5 average rating, 124 reviewsThe Middle Point Cottage at Saint Michaels
Cottage in North Beach
4.97 out of 5 average rating, 105 reviewsBell Estates-Brand New Bay View, Beautiful Cottage
Private cottage rentals
Cottage in Edgewater
4.99 out of 5 average rating, 131 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Cottage in Tracys Landing
4.9 out of 5 average rating, 340 reviewsCharming Waterfront on Chesapeake Bay
Cottage in Cambridge
4.98 out of 5 average rating, 111 reviewsChurch Creek - waterfront cottage & pool - private
Cottage in Saint Michaels
4.98 out of 5 average rating, 434 reviewsSt. Michaels-Historic Dist. Margaret Wells House
Cottage in Colonial Beach
4.83 out of 5 average rating, 143 reviewsSUPERB BEACH COTTAGE- Waterview, firepit, porch!
Cottage in Reedville
4.95 out of 5 average rating, 117 reviewsBull Neck Cottage
Cottage in Reedville
4.9 out of 5 average rating, 173 reviewsChesapeake Bay Beach Cottage
Cottage in Hague
5.0 out of 5 average rating, 86 reviewsPotomac River cheerful cottage
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
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Cottage rentals Maryland
- Cottage rentals Maryland
- Rentals with outdoor seating Southern Maryland
- Rentals with a fireplace Southern Maryland
- House rentals Southern Maryland
- Rentals with a hot tub Southern Maryland
- Bed and breakfasts Southern Maryland
- Smoking-friendly rentals Southern Maryland
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- Pet-friendly rentals Southern Maryland
- Rentals with beach access Southern Maryland
- Rentals with an EV charger Southern Maryland
- Rentals with a firepit Southern Maryland
- Rentals with a kayak Southern Maryland
- Family-friendly rentals Southern Maryland
- Flat rentals Southern Maryland
- Private suite rentals Southern Maryland
- Apartment rentals Southern Maryland
- Rentals with pools Southern Maryland
- Rentals with an accessible-height toilet Southern Maryland
- Rentals with a patio Southern Maryland
- Farm stay rentals Southern Maryland
- Townhouse rentals Southern Maryland
- Rentals with breakfast Southern Maryland
- Rentals with a cinema Southern Maryland
- Beachfront rentals Southern Maryland
- Guest house rentals Southern Maryland
- Rentals with a washing machine and dryer Southern Maryland
- Waterfront rentals Southern Maryland
- Fitness-friendly rentals Southern Maryland
- Rentals with lake access Southern Maryland
- Monthly Rentals Southern Maryland
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