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Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

Spacious Beach House Top Floors - Walk Everywhere!

This booking is for the entire SECOND story & loft of a DUPLEX-style beach house. Entrance, access, & all indoor spaces of the unit are private, however there are often other guests and families on the first floor. There is also a STAIRCASE to the 2nd floor unit and a STAIRCASE to the loft. Please ensure this home suits your needs. The space has an open floor design with 14' cathedral ceilings for a spacious modern feel with beach-house charm. Walk 2 blocks to the beach, boardwalk, and more!

The Wise Quack 2 - A Taste of the Chesapeake Bay!

Welcome to The Wise Quack 2! Take it easy at this unique and tranquil getaway, 1-1/2 blocks to the Chesapeake Bay. In a water-priviledged community with marina, dock and mini-beach front, bring your water toys and get ready to enjoy! Our cozy summer cottage has 2 bedrooms, bathroom, living room, dining room and fully stocked kitchen. Relax outdoors on the screened-in porch or around the fire pit. There’s also a charcoal grill. We are centrally located to activities, shopping and restaurants.

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”). And be sure to visit our sister property, White Point Cottage!

Charming 1BR Bungalow Guest Suite | Close To Water

New construction with separate entrance; 1BR guest suite with a mini bar, a full bathroom with a gorgeous stand up shower & bench. You can see the water from the driveway. Your guest suite was built as a new addition to the classic 1940's bungalows that define North Beach. Tastefully furnished with various artwork displayed throughout the unit. The guest suite is located in North Beach, MD, only several mins walking distance to restaurants, shops, boardwalk pier, beach & Chesapeake Bay.

Waterfront, Dog-friendly, Hot Tub, Peleton

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l dates**

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Charming 4Bdrm 3Bath House 2King beds 1Queen& Bunk

You’ll have the full, 4 bedroom home with 3 full baths in Chesapeake Beach, MD. Less than a mile from the bay. This split level house has a full kitchen, dining room, large deck, family room and a kids bedroom with Captain's Bed (bunk bed with twin over full). Just 4 miles from Herrington on the Bay and North Beach, 3 miles from the Chesapeake Beach boat docks and Rod 'N' Reel Resort, and 31 miles from Annapolis, MD, 39 miles from Washington, DC and 55 miles from Baltimore, MD.

Mid-Century Modern: Direct Private Beach Access

Wake up in the morning to the sounds of seabirds calling and waves lapping on the beach. A huge bank of windows and sliding glass doors makes the Bay the centerpiece of the entire living and kitchen areas. The house draws you outside to enjoy a morning cup of coffee on the veranda, before heading down the stone steps to enjoy a day on the private beach, or you might simply enjoy relaxing with a book in the hammock, while listening to music on our built in speaker system.

Beach Home | King Bds | Firepit | Backyard Dining

Welcome to A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor.

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

Comfy King Bed Home, walk to dinner & beach!

King & Queen Beds Ultra high-speed WiFi Quiet and Very Comfortable Easy 3-block walk to restaurants and the bay, this super comfortable, spacious cottage has a fully-equipped kitchen, workspace, and everything you need for a relaxing stay at the beach! Short drive to nearby wedding venues @ Herrington Harbour South. (2.2 miles)