Holiday rentals with a fire pit in Wicomico County

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

Stunning Home w/Private Pool, Garden & Firepit

Step into this large, recently updated historic home on over 2.5 tranquil acres! Encompassing 3500 sq. ft. with 4BRs & 2BAs, it offers a mix of contemporary and old-world charm. It is 30 minutes from Ocean City & a short drive to downtown Salisbury. The home is named after Bishop William Stone who resided there in the early 1800s. ● Private in-ground large pool ● French inspired parterre garden ● Relaxing, covered porch with rocking chairs ● Slate patio with firepit Many more amenities below!

Peaceful country setting near the Beach

Welcome guest, our small farm is quaint and peaceful with farm life all around us. Birds chirping and horses grazing ( please no petting) Our farm is 15 minutes from Salisbury, Md where we have the Salisbury Zoo, and great restaurants. We are also 30 minutes from Ocean City, Md where we have the famous Thrashers Fries and boardwalk. Assateague National Seashore is also 30 minutes away where you can bike ride, kayack, or just walk the trails. The wild ponies of Assateague are a must see.

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.

Cozy Cottage Hideaway

This memorable place is anything but ordinary. Our tiny cottage was designed for a peaceful retreat or romantic getaway. It has a full-size bed and also a twin in a small loft, that is suitable for a younger child. You can enjoy the peaceful surroundings on the front deck; you may even see some fox, deer, or other wildlife roaming the area. There is also a campfire and picnic area on site. The location is just a short drive to local beaches. This little gem offers the best of both worlds.

Renovated 4 Bed 2 Bath Ranch

Welcome, to your home away from home. This ranch style NEWLY RENOVATED 4 bedroom 2 bath house comes completely furnished. Located in Salisbury Maryland, and 25 minutes from the beautiful beaches of Ocean City and 35 minutes from Rehobeth beach Delaware. 1 hour from Dover Downs Raceway and Casino. Enjoy the local surroundings including the Salisbury Zoo, the Salisbury Mall (1/4 mi away) an array of various restaurants and shops. And Salisbury State University is just 5 miles away.

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.

*Freshly Updated & Clean! Perfect Family Home!*

Built in 1920, this freshly updated two-story home offers the comforts of contemporary living with a bit of historic charm. Located in a quiet neighborhood just 5 mins from downtown & Tidal Health, 7 mins from Salisbury U and just 30 mins from the beach in OC. This property is fully equipped and features new furniture, comfortable bedrooms and an incredible outdoor space your group will surely enjoy. We hope to have the pleasure of welcoming you soon!

Forest Grove Retreat

Quaint two bedroom house situated on a large country lot, fire pit, car port. Centrally located between Salisbury and the Beaches... Ocean City and Assateague Island. Distance to Ocean City and Assateague is about 20-30 minutes. The scenic route to Assateague will take you through Berlin, MD. A beautiful town with lots of restaurants and shopping. The second bedroom is off of the main bedroom, has privacy. We have WiFi! Pets are not allowed

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.

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.