Vacation rentals in Sharptown

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

Hot Tub | Mini Golf | Arcade | Gym — Coastal Quad

Welcome to The Coastal Quad, New Jersey’s first pocket resort! You will be booking a stay in one of four luxurious, 1BR tiny cottage suites, so each visit is a new adventure! You will enjoy your own private hot tub, fire pit, grill, fenced-in yard, and access to a shared rooftop mini golf course, retro arcade, full gym with sauna, office, laundry facility and more. Located just steps from a quiet bay beach and a short drive to Cape May and Wildwood, this is the most exciting resort at the shore!

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)

Nature retreat with water view

Welcome to this cozy updated two bedroom, one bathroom single family home with a water view of the Nanticoke River. Enjoy the wrap around porch, with gazebo, fire pit, outdoor shower, sink and grill. Sit on the porch and feel the breeze from the river, or walk across the street to enjoy the beach or the covered pavilion. Great area for bike riding, kayaking, paddle boarding, and windsurfing. Public marina, tennis courts and additional public beaches are minutes away.

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.

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.

4bed/4.5bath Lux Farmhouse/Pool/Gym/5 min from SU

BEFORE BOOKING: Pool will be open 4/05/26 Unless PRIOR AUTHORIZATION….. NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your party are allowed on the property. Fully restored top to bottom 1920s farm house. Every bedroom has its own full bathroom Full laundry room with extra refrigerator RH furniture All bedding/towels/paper towels/toilet paper/body wash/shampoo/conditioner/spices/laundry detergent included;Total turn key

Waterfront Barn Loft with Modern Cabin Vibe

Relax in nature for a while in our beautiful and cozy barn loft. The loft is located next to our primary residence on 7 private acres along scenic Rewastico Creek, offering year round beauty. Kayak on, or relax by, the tidal marsh creek which is fed by the Nanticoke River and Chesapeake Bay. Centrally located between popular Eastern Shore destinations such as Atlantic beaches and historic small towns. A serene oasis with abundant wildlife.

High St. Art Gallery Suite

This boutique suite is adjoined to the future home of High St. Art Gallery. This historic home was built in 1796 and is being lovingly restored by three generations of a family committed to creating beautiful, unique and comfortable spaces that can be a retreat away from home. This suite has all the details and delights that will make your stay enjoyable and we hope you will come again and again.

Highbanks House

Forget your worries in this spacious and serene space. Welcome to your dream home! This stunning 5-bedroom, 3-full-bath rancher is nestled on over 6 acres of private land, offering a perfect blend of comfort and nature. Located just 6 miles from downtown Salisbury and 8 miles from Salisbury University, this property provides both tranquility and convenience.

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

Wigwam Lodge is an experience nestled in a pine & hard wood forest with rural privacy. Incredibly spacious decks. Surround Forest Views inside and out! 5-min from Choptank river, 20-min from Historic Denton, Irish Pub & Grocery, 1hr from the beach. Easy PARKING 10ft from the front door. Solid WIFI! Click “Show More” Below to SEE ALL Deets...