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Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Custom waterfront home with everything you need to relax and recharge. Two levels of decks offer amazing views of the changing tides on Cat Creek. Soak in the hot tub and watch the eagles soar by, or head down to the dock for crabbing, fishing, and kayaking during high tide. Located in historic Southern Maryland, this quiet, hidden estuary makes for a unique getaway with great amenities. Fast WiFi for work, game room for fun, and a fenced-in yard for dogs. 1 hour from DC but feels worlds away.

Tranquility on Tilghman Island – Wide Water Views

Wake up to sweeping waterfront views, spend your days crabbing from your private dock, kayaking along the shore, or lounging by the pool with a good book. Just minutes from charming St. Michaels, this 4-bedroom retreat blends coastal charm with modern comfort — perfect for families, friends, or a romantic getaway. In the evenings, grill, gather around the firepit under the stars, and let the day fade away in the bubbling hot tub. Guests love the spacious layout, the dreamy screened-in porch for

Hot Tub Hideaway by Shark Tooth Shores

With views of the Chesapeake Bay, access to private beaches, a brand new hot tub, air hockey table, kayaks, and being just minutes away from hot spots like Calvert Cliffs and Solomon's Island the Hollow makes for the perfect vacation destination. Enjoy sunrise views through the treetops each morning on the expansive back deck, or use our eco-friendly wood burning stove for autumn and winter nights. Unlike many beach houses, this home is surrounded by trees making it serene. UPDATED PHOTOS SOON

Blue Pearl-Luxury estate with private dock/jacuzzi

The Blue Pearl is a luxurious river front estate with a private pier to catch crabs, fish and kayak. Soak in the outdoor jacuzzi and enjoy the river life. Three bedrooms with three full bath en-suites and over 2800 square feet of luxury accommodations await you. Office has Queen sleeper sofa. Pull up to your private boat dock, catch blue crabs with the provided traps, toast s’mores in the firepit while sitting in your Adirondack chairs. Enjoy two decks to view the sunrises and sunsets.

Private, Lakefront Oasis- Lavinia by the Lake

This home is the embodiment of true Southern Maryland waterfront living. It is the best location for Rockfish, crabbing and oystering!The house is fully gated so you will always have peace of mind while your kids and pets wander around. This 5 bedroom, 3 bathroom stunner with a full walk out basement is perfect for the larger water loving family who loves to entertain. The outdoor living space hits all the marks: upper and lower deck, umbrellas throughout, a Gazebo bar, Hot Tub and more.

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

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**

Grand Tudor Home w/ Saltwater Pool & Hot Tub

Welcome to our Grand Tudor Home, a peaceful retreat where families and friends can relax, reconnect, and create lasting memories. Nestled on 3 acres, this elegant 5-bedroom, 3.5-bath home offers approximately 4,700 sq ft of beautifully designed living space with a private saltwater pool (June–September), year-round hot tub, gourmet kitchen, and spacious gathering areas. Minutes from Chesapeake & North Beach, easy driving distance to Solomons Island, Annapolis, and Washington, DC.

Marina View Getaway | 3bd 2.5 bath

Walk, don‘t drive to Herrington Harbour Marina, a beautiful wedding venue and local waterfront restaurant, bar, and deli market. This charming single family home with spacious backyard and hot tub, is perfect for an unforgettable experience in North Beach, MD. Enjoy a clean and cozy stay walking distance from Herrington Harbour’s amenities and a short drive to downtown North Beach and Chesapeake Beach. No better way to relax than a marina view getaway!

Private Pool + Spa Retreat | Maryland Crab Feasts

Welcome to your private Southern Maryland retreat, where pool days, Maryland crab feasts, wedding weekends, and family gatherings come together. Relax by the pool and spa, gather around the fire pit, fire up the grill, or enjoy a Crab Feast. Minutes from Solomons Island, Calvert County wedding venues, Calvert Cliffs, and nearby military installations. Note to guests from the city: The house is located in the country there are pests and bugs.

Swaggers Point Lake front Retreat

Relax at our peaceful waterfront Solomons retreat with a private dock, hot tub, and beautiful sunset views. We provide everything you need, including kayaks, fishing poles, crab traps, nets, life vests, crabbing gear, premium linens, spa-quality toiletries, a fully stocked kitchen, coffee bar, Wi-Fi, and smart TVs. Every stay includes our signature Chesapeake Welcome Basket with local treats. Just arrive, unwind, and enjoy the Bay!

Studio on the Bay.

This studio apartment is in walking or driving distance to three private beaches in our community. There is 1 bedroom with a queen size bed, spacious bathroom and closet. The living room has a pull out full size bed and a kitchenette. Coffee, teas, beach chairs, are provided. Wanna fish??? Ask Joey about Fish Taxi! Fifteen minutes from Solomons Island (home of the Tiki Bar). An hour or so from DC, Annapolis and Waldorf.

Bayfront Walk-Out Beach Home | Sunrise & Fire Pit

Wake up to sunrise views over the Chesapeake Bay in this true walk-out beach home. Step directly from the property onto a sandy, shallow shoreline via short, easy steps. The bayfront beach is ideal for wading, exploring, and spending time together by the water. This modern Panabode log cabin blends rustic charm with clean, contemporary comfort. Relax on the deck, in the hot tub, by the fire pit, or on the sand.