Vacation rentals in Princess Anne

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Top-rated vacation rentals in Princess Anne

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Guest favorite

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, 361 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.

Superhost

An open kitchen and dining area are visible, featuring white cabinetry and stainless steel appliances. A large table with a light green tablecloth is surrounded by dark green chairs. The space includes a cozy living area with a textured rug, enhancing the inviting layout.

Loft in Salisbury

4.83 out of 5 average rating, 103 reviews

Deluxe corner apartment with riverfront views

This corner apartment features high ceilings, exposed brick, 9 windows with riverfront views, 2 cozy bedrooms and a grand open kitchen complete with a large island and dining area that flows into an open living room filled with natural light. With classic design touches as well as modern features you’ll be sure to appreciate the beauty as well as the views and convenience. It features a full kitchen with an island, tile and hardwood floaring, 2 comfortable bedrooms and an updated bathroom.

Top guest favorite

A spacious driveway leads to the entrance of a one-bedroom apartment. The light-colored building features a pair of windows flanking a central door. A large, open grassy area extends beyond the driveway, bordered by trees in the background.

Apartment in Salisbury

4.91 out of 5 average rating, 193 reviews

Private Luxurious One Bedroom Apartment

My place offers a 30-minute drive (may vary) to Ocean City beaches, and less than a 10-minute drive to the Zoological Park, downtown Salisbury, and nice restaurants. You’ll love my place because of the comfy bed, a large driveway, a large backyard for outdoor activities, and its location in a very quiet residential neighborhood. The luxurious one-bedroom apartment is good for couples, solo adventurers, couples with one kid, and business travelers. People from all backgrounds are welcome.

Guest favorite

A comfortable beige sofa is positioned against a light-colored wall. It features decorative cushions with intricate patterns. A small lamp on an adjacent table provides soft illumination, enhancing the cozy setting. A plant is placed nearby, adding a touch of greenery to the area.

Loft in Salisbury

4.95 out of 5 average rating, 129 reviews

Tree Top Loft

Studio apartment is located on a wooded lot in a quiet neighborhood within 4 miles of Salisbury University & Downtown! Off street parking at entrance patio & a flight of stairs leads up to the apartment, which includes a queen size bed, full kitchen with full size refrigerator, 4 burner electric stove, full size washer and dryer. Bathroom includes shower, toilet and vanity, perfect for a week or weekend stay! We are located near Ocean City, Maryland, Assateague National Seashore.

Top guest favorite

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, 214 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.

Guest favorite

A bright living area features wooden beams and large windows adorned with plaid curtains. A variety of cushions decorate a sectional sofa and a leather couch. A television offers a view of a sports event, while an area rug adds pattern to the wooden floor.

Farm stay in Princess Anne

4.94 out of 5 average rating, 108 reviews

Farmhouse located on a horse farm

Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

Top guest favorite

A modern barn-style exterior is shown with a soft twilight glow. Inside, a cozy loft bedroom features a spacious bed adorned with decorative pillows. A bright dining area is visible, highlighting wooden accents and seating. Two playful goats are seen exploring their cozy enclosure.

Loft in Pocomoke City

4.99 out of 5 average rating, 101 reviews

Cozy Barn Loft: Country Views & Central to Beaches

Relax and recharge as you soak in the country views while enjoying this cozy space. A private entrance leads upstairs to the loft, located above our renovated barn. Enjoy your days at the beach, boating, fishing, birding, and more. Return home to be greeted by goats as you pull in the drive. Coffee, tea, and farm fresh eggs will be waiting for your arrival. Centrally located between the beaches of Chincoteague, Va and Ocean City, MD. Beach gear provided as well.

Guest favorite

An open-concept living area is highlighted by a combination of seating options, including a brown sofa and an ottoman. The kitchen is equipped with dark cabinetry and a breakfast bar. Light filters through patterned curtains, adding a soft ambiance to the space.

Home in Salisbury

4.91 out of 5 average rating, 107 reviews

Brand new 2 story condo. Relaxing area

Central location behind centre of Salisbury, route 50 and 13, by the Salisbury zoo, downtown salisbury, tidal health health institution,… 30 min from oc md and assateague. area has dog and kid park to play. Residence has 3 bedroom, 2.5 bath, living room has fold out couch. large keyboard, darts, foosball, cards, jenga, other board games available . FYI I have a dog and we stay in the house, cats are invited too so those with allergies be aware

Guest favorite

The exterior of a two-story house is shown, featuring a light-colored façade and multiple windows. A staircase leads to an entrance at the front. A well-maintained lawn surrounds the structure, and a friendly corgi is visible on the grass.

Guest suite in Crisfield

4.76 out of 5 average rating, 225 reviews

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

Top guest favorite

A rustic barn loft is nestled among trees, featuring a welcoming staircase leading to the upper deck. Soft lights illuminate the entrance, enhancing the natural surroundings. The gravel driveway and landscaped area provide convenient access to the property, highlighting its serene setting.

Loft in Hebron

5 out of 5 average rating, 106 reviews

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.

Superhost

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

4.82 out of 5 average rating, 155 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.

Superhost

A private retreat is visible with two houses positioned along a sandy beach. A wooden pier extends toward the water. Lush green trees frame the property, providing a serene atmosphere. The main house features a spacious facade, while the guest house presents a charming design, both overlooking the waterfront.

Villa in Princess Anne

4.8 out of 5 average rating, 147 reviews

Waterfront Retreat & Guest House

Enjoy a relaxing private retreat with an amazing view of the water. Come to stay at the house the whole time enjoying sunsets, kayaking, building sand castles, playing in the water, and making great meals or venture to many nearby towns with great restaurants, hikes, golfing, breweries, bike paths, and more. Enjoy your own private 100 ft pier and sandy beach. **great wifi in main house and guesthouse