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The Whole Fam-damily

Charming Historic Home with Porch, Yard & Convenient Location Step into timeless charm and comfort at this beautifully preserved 1927 home in the heart of historic Hebron. Perfect for families, couples, or small groups, this inviting retreat offers the cozy feel of small-town living with the modern comforts you need for a relaxing stay. Start your mornings on the shaded front porch with a fresh cup of coffee, or unwind in the evenings as you watch the neighborhood come to life. The fully fenced backyard gives kids plenty of space to play freely, while adults can relax and enjoy the peaceful surroundings. This is the kind of place where you can truly slow down and enjoy the simple moments. Located in a highly convenient area, you are steps from the local park, tennis courts, and seasonal community events like the Hebron Volunteer Fire Department carnival and Fourth of July fireworks. When you’re ready to explore beyond town, you’re perfectly positioned on Maryland’s Eastern Shore— just a short drive to Salisbury (7 miles), Ocean City’s sandy beaches (36 miles), and the wild ponies of Assateague Island (38 miles). You’ll also find scenic waterfront spots like Cove Beach Park and Roaring Point Park nearby, offering perfect sunset views. Inside, the home blends historic character with modern convenience. You’ll notice the charm in every detail—from the original creaks of the floors to the welcoming, well-loved furnishings. The spacious layout includes a comfortable living area with plenty of seating, and each bedroom (plus the living room) features a Smart TV with access to your own streaming services as well as over 250 free channels. The home offers a bright eat-in kitchen, a separate dining room for shared meals, and a main-floor primary suite with a private bathroom for added convenience. Upstairs, you’ll find three additional bedrooms and a full bathroom, making this home ideal for families or groups. Additional amenities include complimentary WiFi, a laundry room, and thoughtful extras like a beach bag stocked with towels and a blanket—perfect for spontaneous coastal day trips. Whether you’re here to relax, explore, or reconnect, this charming Hebron home offers a warm, welcoming stay you won’t forget. Things to Know: - Check-in: 4:00 PM | Check-out: 12:00 PM - Smart TVs in living room and all bedrooms with free channels + streaming (use your own accounts) - Free parking (3 vehicles in drive, unlimited street parking) - No pets allowed - No smoking in the house - Quiet hours: 11:00 PM – 8:00 AM - Must be 25+ to book - Ring camera at side entrance (main guest access) - Locally hosted with 24/7 guest support - ID must be presented to Ring camera at check-in and must match reservation to obtain YALE code

4 bdrm, 3 bath, 2,700 sqft whole house on 1 acre

Bring the whole family to my spacious house. 3 bathrooms for everyone to get ready. 2 king beds and 2 queen beds across 4 bedrooms. Huge living room, kitchen, and dinning room. Enjoy a sun room and fenced in back yard. Fresh eggs from backyard chickens. Merry Maids regularly cleans the bathrooms and kitchen. The basement, garage, and shed are for storage, and are not part of the rental. While quiet just outside of the city, there maybe some highway noise or farm animal noise. Large driveway

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Charming Home in a Neighborhood

Our home is well loved and is a great place to spend some quality family time. It is close to the Salisbury Airport (SBY), Salisbury University (SU), Perdue Stadium (Delmarva Shorebirds) and short drives to University of Maryland Eastern Shore (UMES), the beaches in Ocean City MD, Asseteauge Island, Md and some Delaware beaches too. Winterplace Equestrian Park is within 4 miles and Pemberton Historical Park is just across town. Price includes parking in the attached oversized 2 car garage.

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

1900's Modern Farmhouse on 7.5 private acres

Welcome to our 1900's farmhouse. This home has been lovingly updated and maintained over the past century, and sits on 7.5 acres. While it is private and peaceful, its location is minutes away from everything making it easy to get around. Enjoy spacious living and endless outdoor fun in our dedicated game barn (ping pong, cornhole!) and large pastures (frisbee golf, soccer!). This family-friendly home blends historic charm with modern comforts, perfect for creating unforgettable memories.

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

Salisbury Cottage

Relax in a quiet part of Salisbury in this cozy, 3 bedroom, 2 full bath home. A farmhouse feel welcomes you home after a long day at work, a sports trip, or vacation. Enjoy all new furniture including luxury bedding and smart TVs. Centrally located and close to downtown for shopping and dining at one of the many local restaurants. Only 30 minutes from the beaches of Ocean City & Assateague Island. One mile from Tidal Health PRMC and a half block away from Salisbury University.

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

Tiny House on Maypop Homestead

Welcome to Maypop Homestead, our peaceful 14-acre retreat in historic San Domingo. Stay in a cozy tiny house surrounded by a lush forest and a wildlife-filled pond. Enjoy a queen bed, kitchenette, full bath with a composting toilet, meditation loft, Wi-Fi, and a large deck with a fire pit. We grow organic food, medicinal herbs, and flowers—tours and seasonal harvests available! Meet our friendly cats and relax in nature. Come enjoy a quiet, earthy escape.

Stella

Welcome to Stella! She has been lovingly restored by our family and carefully designed by our son who owns JoonMoon Design with his beautiful wife. We are a family who loves to travel and discover places of rest. Stella was designed with that in mind. She is approachable, comfortable and invites you to kick off your shoes and relax. She is walking distance to Salisbury University and close to many restaurants and stores.

Rumbley Cottage on the Tangier Sound-Private Beach

September 12-16 available. Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.