Holiday houses in Hebron

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

Location · Family · Condition

Johnna's House

Two story dwelling in a prime location on the Eastern Shore of Maryland. It is conveniently located 32 miles from Ocean City. It is equipped with central air and heat, a two car garage, WiFi and cable. It is centrally located and is within walking distance of eateries and Super Wal-Mart. Pharmacies are in close proximity. It is also in walking distance from the local college, Salisbury University. And is less than a 1/2 mile from Salisbury City Limits. The local mall is only a 10 minute drive.

Location · Value · Long stay

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.

Location · Value · Bathroom

The Red Maple Studio minutes from Salisbury!

Red Maple Studio is a private 1‑bedroom studio on a quiet street in historic Delmar, MD. Kylan Barn – 6 min. Venue 54 – 7 min. Downtown Salisbury – 15 min. SU – 20 min. OCMD – 45 min. Sleeps 4 with king bed and pull‑out couch. Workspace, fast WiFi, kitchenette (no cooking), private laundry. Safe neighborhood, off‑street parking, well‑lit walkways. Private backyard patio with 6’ fence. Stylish, super clean and comfortable. Sorry….no 3rd‑party bookings, pets, parties, indoor smoking or cooking.

Location · Value · Backyard

Havana Hideaway

Havana Hideaway offers a charming and unique retreat inspired by the vibrant culture of Cuba, capturing the essence of Havana through its decor and ambiance. As you climb the stairs to its entrance above the barn, you are treated to beautiful pastoral sights. Inside, you are greeted by colorful and tropical-inspired decor that immediately transports you to a Cuban paradise. After a day in town or neighboring beaches, you can return to your tropical retreat and unwind on the private balcony.

Value · Location · Indoor spaces

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.

Value · Family · Condition

Amazingly convenient yet secluded.

Our place has views; the yard has beautiful shade trees that set the mood for deep relaxation. One can walk to Walmart, Denny's, Hampton Inn Suites, Ruby Tuesdays and many other business's in minutes. Ocean City is about a 35minute drive. Salisbury University is a five minute drive. UMES is a 13 minute drive.This home is ideally located. A retired teacher on one side is your closest neighbor; on the other property is a caregiver. Needless to say this is a very safe place; enjoy.

Value · Family · Sleep quality

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.

Value · Location · Solo travel

Beautiful Renovated Home, Perfect Getaway!

Enjoy your stay in the quaint part of Salisbury in this cozy, newly renovated 2 bedroom home. A lovely space to unwind and relax after a busy day whether it is work or play. Awake refreshed and ready for a day of exploring. Head out and wander through the quiet neighborhood, bike to downtown Salisbury to do a little shopping and enjoy the local foods. We are 30 minutes from the sandy beaches of Ocean City & Assateague Island and 1 block away from Salisbury University.

Location · Value · Backyard

Deluxe corner apartment with riverfront views

This corner loft apartment features high ceilings, exposed brick, 9 windows with river views, 2 bedrooms and an open kitchen complete with a large island and dining area that flows into a living room filled with natural light. In the living room you will find a 55" TV, love seat, fold-out couch and futon. With classic design touches as well as modern features you’ll be sure to appreciate the beauty as well as the views and convenience. 

Value · Family · Parking

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

BEFORE BOOKING: Pool will be open 4/05/26 NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your reservation 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

Value · Family · Check-in

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.

Value · Family · Layout