
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

Waterfront Cottage & Guesthouse Near Cambridge

Riverside Haven w/ Hot Tub

Cozy Cottage close to Beaches & Solomon’s Island

Luxury Cottage | Hot Tub & Quiet Oasis Near DC

Bay cottage 🏖on the beach. Stunning views🏝

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

Hot Tub Hideaway by Shark Tooth Shores
Pet-friendly cottage rentals

The Little Anchor Cottage, St. Michaels, MD

“Little Sligo” Historic Downtown Cottage Near I-95

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Modern 2 Bdrm Cottage in Historic River Community

Rockhold Creek Cottage

Bungalow Private Beach & Dock Colonial Beach Water

THE PRINCE COTTAGE WITH PRIVATE PARKING GARAGE!!!

Bell Estates I Beautiful Cottage I *Beach Passes*
Private cottage rentals

Waterfront Cottage with Beautiful Sunset Views

Relaxing Waterfront Cottage w/ Private Dock/Kayaks

The Colonial Cottage of Alexandria

Cozy Cottage on the Bay

Levering Creek Cottage with Private Dock

Welcome To The Overlook!

Loon Cottage on Leeds Creek

Elk Cottage-Lake Lariat / Private lake access
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- Outer Banks Holiday rentals
- The Hamptons Holiday rentals
- Guest house rentals Southern Maryland
- Rentals with a washing machine and dryer Southern Maryland
- Pet-friendly rentals Southern Maryland
- Rentals with a fireplace Southern Maryland
- Rentals with pools Southern Maryland
- Smoking-friendly rentals Southern Maryland
- Apartment rentals Southern Maryland
- Rentals with beach access Southern Maryland
- Rentals with a patio Southern Maryland
- Family-friendly rentals Southern Maryland
- Private suite rentals Southern Maryland
- Bed and breakfasts Southern Maryland
- Townhouse rentals Southern Maryland
- Beachfront rentals Southern Maryland
- Rentals with breakfast Southern Maryland
- Rentals with a hot tub Southern Maryland
- Rentals with an EV charger Southern Maryland
- Rentals with a firepit Southern Maryland
- Waterfront rentals Southern Maryland
- Rentals with lake access Southern Maryland
- Flat rentals Southern Maryland
- Farm stay rentals Southern Maryland
- Cabin rentals Southern Maryland
- House rentals Southern Maryland
- Rentals with an accessible-height toilet Southern Maryland
- Rentals with a cinema Southern Maryland
- Rentals with outdoor seating Southern Maryland
- Fitness-friendly rentals Southern Maryland
- Rentals with a kayak Southern Maryland
- Cottage rentals Maryland
- Cottage rentals United States
- Nationals Park
- The White House
- National Mall
- Georgetown University
- District Wharf
- Smithsonian National Museum of Natural History
- National Museum of African American History and Culture
- Sandy Point State Park
- Arlington National Cemetery
- Georgetown Waterfront Park
- Six Flags America
- Washington Monument
- Great Falls Park
- National Harbor
- Smithsonian American Art Museum
- Library of Congress
- Lincoln Park
- The Pentagon
- Breezy Point Beach & Campground
- Piney Point Beach
- Quiet Waters Park
- American African Museum
- Meridian Hill Park
- Chesapeake Beach Water Park