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Waterfront Home with Private Beach, Stunning Views

Escape to paradise at our Chesapeake Bay waterfront vacation home in Oliver Beach! Our home is the ideal place to unwind and appreciate the beauty of Chesapeake Bay. You'll love the stunning views, the private beach, the spacious upper deck and the beachside deck surrounded by trees. You'll have so much fun fishing, swimming, kayaking, paddle boarding, or just relaxing by the water! It's the perfect spot for a dreamy retreat, a romantic sojourn, or for shared fun with group of friends or family.

The Little House of Rockaway Beach, Maryland

Unwind at this new home in a quiet, safe neighborhood on the Chesapeake Bay. Designed by the host, the house is decorated with a mix of vintage and new items lovingly chosen to create an eclectic coastal cottage. Four adults (no pets) will sleep comfortably on a queen bed and a sleep sofa w/queen mattress. The clean and modern kitchen is fully equipped. Enjoy water views from the attached deck or walk a short distance to the waterfront where a designated deck offers seating and water sport gear.

Sue Creek Waterfront Cottage

Kick back & relax on the water in a fully renovated private 2 story home w/ a dedicated pier located on Sue Creek on the Chesapeake Bay! Includes 2 master bedrooms each with a queen size bed and dedicated bathroom with large shower stall. Kitchen & Great room are fully equipped with all amenities for a comfortable stay. Outside includes a large patio with furniture and charcoal grill, a pier w/ 2 Kayaks & private parking area. Convenient to many water & land establishments! No Pets or smokin

Charming Havre de Grace Home Walk to Downtown

This charming 3-bedroom, 2-bathroom home in historic Havre de Grace is the perfect mix of perfect location and relaxing getaway. Easily stroll to shopping, restaurants and nightlife in downtown Havre de Grace, or take a kayak down to the Susquehanna River. Three private bedrooms feature a king bed, queen bed, and twin bed. One bathroom has a tub-shower combo and the other has a stand-up shower. Kitchen has all major appliances and gadgets. Parking is free and plentiful. It doesn't get better!

Serenity on the Cove

Escape to the serenity of Oakleigh Cove! This beautiful A-Frame waterfront home is the perfect getaway for water lovers! It even has its own pier, crab pots for seasonal crabbing, and outdoor living space with games!, We even rent out boat slips for our guests with their own watercraft! You will be required to digitally sign an additional rental agreement before your stay. Note: If your stay is longer than 30 days, we will have the place cleaned monthly at an additional $245 per month.

Luxury, Modern 2-Bedroom Water Front Apartment!

Private waterfront oasis. Luxury 2 bedroom with stunning water views. Porcelain tile floors & granite countertops in a fully equipped kitchen; comfortable furnishings in main living area. Bathroom features a double jacuzzi tub/steam shower. The private deck is perfect for morning coffee & evening cocktails. Dock space for boat/water toys. Kayaks & paddleboards with tiki bar right across river. Private gym, golf putting/driving areas, ping pong, pool tables, basketball. Private hot tub.

Rumsey Island!

This beautiful home has a fenced in backyard and views from the backyard that leads out to Chesapeake bay. Variety of fish to catch off the dock. Many local hiking trails and beautiful state parks. Many stores near by and within 2-15 mins you have a variety of stores in all directions. Bring the whole family or just a guys trip to fish or possibly a girls weekend to get some rest. This home has the views and the feels for a getaway. Look no further Chesapeake bay is a boat ride away.

Chesapeake Getaway | Marinas | Woodland Views

Escape to our peaceful retreat on Maryland's Eastern Shore, nestled in a quiet, wooded neighborhood near historic Chestertown. The Chesapeake Bay is known for its wildlife and serene landscapes. This cozy haven is perfect for unwinding and reconnecting with nature. After exploring Chestertown's charming streets, local shops, and delightful restaurants, or kayaking at nearby Worton Creek, relax in our comfortable home, where you can read, play games, or enjoy the peaceful surroundings.

East Baker Bungalow

Welcome to our home away from home on Bush River! Relax and unwind overlooking the beautiful water where you can bring your own boat. Whether you're here for the weekend to escape the hustle and bustle or bringing all your family and friends for a week on the water, we have something for everyone! Bring your own Boat, kayak or even fishing off your own private pier. Only 40 minutes from Baltimore's airport, 15 minutes to Ripken Stadium and super close to shops and grocery stores!

Waterfront Family Vacation Home

Relax and unwind in this completely remodeled waterfront vacation home, perfect for family and friends. It boasts four spacious bedrooms, three full bathrooms, a cozy den, a sunroom, a large patio, and an expansive outdoor space. It provides a stunning view of the Bush River and sunsets, with direct access to the water. Immerse yourself in nature’s beauty with kayaks, paddle boards, a fire pit, and outdoor grills/furniture. Perfect place to stay for sports tournaments, too!

Waterfront retreat with private dock and kayaks

Unwind at Mill Creek House, a private two-bedroom waterfront retreat just 15 minutes from historic Chestertown. Launch one of four kayaks from the private dock, watch sunsets over the conserved shoreline, and spot bald eagles and ospreys from nearly every room. Inside, enjoy a king bedroom, a queen bedroom, central air, fast Wi-Fi, a full kitchen, a screened porch, a gas grill, and a Tesla Universal Wall Connector that works with both Tesla and non-Tesla electric vehicles.

Cabin on the Creek ~ Kayaks and Fire Pit

Unwind in our cabin tucked away on a private lane mins from Chestertown. We are situated on 6.5 wooded acres, perched up on 100’ bluff overlooking Churn Creek, a tributary off the Chesapeake Bay. Idyllic water views framed by a canopy of oak trees. Enjoy nature as you relax outside by the fire pit or stroll down to the ‘point’ to take in wildlife, or take a kayak out to explore the creek and water fowl. Deer come up through the woods and are often spotted on the property.