Holiday rentals in Wicomico County

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Top-rated holiday rentals in Wicomico County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior of a two-story home is depicted, showcasing a combination of brick and white siding. A well-maintained lawn with green grass surrounds the house. The design features dormer windows, a central front door, and traditional shutters, contributing to a classic architectural style.
Home in Fruitland
4.97 out of 5 average rating, 408 reviews

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.

Top guest favourite
The exterior of the home is showcased with a well-maintained lawn, framed by flowering shrubs. A welcoming front porch is visible, featuring two wooden benches. The entrance is highlighted by a maroon door, accompanied by classic shutters on the windows.
Home in Parsonsburg
4.99 out of 5 average rating, 180 reviews

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.

Top guest favourite
A bright living area features a cozy sofa facing a large arched window, with natural light illuminating the space. A wooden round table is placed nearby, alongside decorative plants. Neutral-colored curtains frame the window, creating a warm and inviting environment.
Guest suite in Salisbury
4.99 out of 5 average rating, 113 reviews

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.

Top guest favourite
A spacious deck features a round table surrounded by six chairs, shaded by a blue and white striped umbrella. Lush greenery borders the area, with views of the tranquil river and trees in the background, enhancing the outdoor experience.
Home in Salisbury
4.93 out of 5 average rating, 56 reviews

The River House

The River House is a historic 1938 cape cod, with a stylish sailing theme, in a peaceful waterfront setting. It is centrally-located on Delmarva, with easy day trips to explore in every direction—St. Michael’s, Berlin, and Cape Saint May to name a few. It is close to restaurants, Salisbury University, Tidal Health, and downtown Salisbury. Ocean City and Assateague National Park are easy to reach in 30 to 45 minutes. The huge deck and adjoining covered area make it easy to enjoy the view.

Guest favourite
An attic bedroom features two spacious beds, each adorned with warm-toned pillows and throws. Bright overhead lights accentuate the light-colored walls and wooden floor, while a decorative area rug adds texture. A window provides natural light, enhancing the peaceful atmosphere.
Home in Salisbury
4.93 out of 5 average rating, 140 reviews

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.

Top guest favourite
A bright kitchen and dining area is revealed, featuring a table with two chairs positioned beneath a window. The space includes light wood flooring, a kitchenette with modern appliances, and various seating options. Natural light filters in through a partially covered window.
Home in Fruitland
4.97 out of 5 average rating, 155 reviews

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.

Guest favourite
A spacious living area features soft, neutral carpeting and modern furnishings. A large flat-screen TV is mounted on the wall, providing entertainment options. Two comfortable armchairs and a cozy sofa are arranged around a wooden coffee table, while a dining area is visible in the background.
Home in Salisbury
4.99 out of 5 average rating, 261 reviews

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.

Superhost
Loft in Salisbury
4.84 out of 5 average rating, 153 reviews

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. 

Superhost
A well-appointed bedroom features a wooden bed with soft green linens and decorative pillows. A bedside table with drawers holds a vintage clock and a decorative object. A woven light fixture hangs above, and natural light filters through the window covered by blinds.
Home in Salisbury
4.9 out of 5 average rating, 143 reviews

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.

Guest favourite
A cozy seating area features a light-colored couch adorned with decorative pillows. A woven coffee table rests on a natural fiber rug, while a window nook is lined with plants, allowing natural light to brighten the space. Wooden accents add a warm touch.
Tiny home in Salisbury
4.84 out of 5 average rating, 249 reviews

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

Top guest favourite
The exterior of the guesthouse is characterized by a light gray facade and two garage doors, framed by planters with green foliage. The enclosed yard is secured by white fencing, creating a private outdoor space.
Flat in Salisbury
4.93 out of 5 average rating, 245 reviews

Cozy Modern Escape w/ Private Patio

Looking for a peaceful getaway? This stylish guest home offers the perfect mix of modern comfort and quiet relaxation. Enjoy a fully equipped kitchen, cozy living spaces, high-speed internet, and a private atmosphere perfect for couples, families, work trips, or weekend escapes. Conveniently located near local attractions while still giving you that peaceful retreat feeling.

Guest favourite
A tranquil pond is framed by natural stone, featuring a gentle waterfall surrounded by lush greenery. Bright flowering plants and a manicured lawn lead to a serene outdoor seating area overlooking the water, offering a peaceful retreat in nature.
Home in Salisbury
4.83 out of 5 average rating, 180 reviews

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.

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