Holiday rentals with outdoor seating in Wicomico County

4.98 out of 5 average rating, 98 reviews

Home in Parsonsburg

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.

5 out of 5 average rating, 105 reviews

Guest suite in Delmar

The Red Maple Studio minutes from Salisbury!

Red Maple Studio is a private 1 bedroom studio centered 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). Queen bed and full size pull-out couch. Workspace, fast WIFI, kitchenette, private laundry. Safe neighborhood, off-street parking, well lit walkways. Inviting backyard patio with 6' tall privacy fence all just for you. Stylish, super clean and comfortable. Sorry no pets or smoking.

4.99 out of 5 average rating, 69 reviews

Guest suite in Salisbury

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.

4.95 out of 5 average rating, 123 reviews

Loft in Salisbury

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.

4.98 out of 5 average rating, 200 reviews

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.

5 out of 5 average rating, 79 reviews

Home in Fruitland

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

BEFORE BOOKING: Pool is open as of 04/5/25 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

4.9 out of 5 average rating, 100 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

5 out of 5 average rating, 103 reviews

Loft in Hebron

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.

4.85 out of 5 average rating, 136 reviews

Tiny home in Salisbury

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.

5 out of 5 average rating, 76 reviews

Salisbury Hideaway

Relax in a quiet part of Salisbury in this cozy, newly renovated 2 bedroom, 1.5 bath home. A modern 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.

Superhost

Cottage in Tyaskin

4.86 out of 5 average rating, 106 reviews

Charming Cottage in Tyaskin, MD

Charming New England salt box style cedar sided cottage directly across from Tyaskin Park. The Cottage is larger inside than appears on the exterior due to vaulted ceilings in the living room, kitchen/ dining areas. Beautiful views of the Nanticoke river from the living room, dining area and large deck. Pine flooring in all rooms with the exception of the tile floor bath and carpeted loft.

4.87 out of 5 average rating, 123 reviews

Hudson House

2400 sq. ft. rancher within walking distance of downtown Salisbury. Short drive to shopping. Quiet neighborhood. 30 miles to Ocean City beach & boardwalk. Hudson House is a destination not a stop along the way! All the comforts of home! House has numerous antiques and curios from the past!

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Holiday House Rentals with Outdoor Seating

4.9 out of 5 average rating, 48 reviews

Cheerful, quiet 5 bedroom home

KimberlyRating, 5 stars3 weeks ago

We had 8 adults and 5 children coming for a family wedding and the house was big enough for us and much more comfortable and economical than a hotel. I had a lot of questions and Bryan and Chrisdy were always responsive and helpful!

4.83 out of 5 average rating, 89 reviews

Renovated 4 Bed 2 Bath Ranch

KristiRating, 5 stars4 weeks ago

This was our second time at Toni's place and it was even better than the first time. The house was just perfect for our stay for our son's College Graduation. You will not be disappointed. We will be back again in the fall.

5 out of 5 average rating, 20 reviews

Spacious 5 bedroom w game room, theatre, and sauna

RhiannonRating, 5 stars1 month ago

This house had it all!!! Super clean and very spacious. The third floor gaming room made my 13 year old feel right at home and we all enjoyed the theater room. The host even provided popcorn and coffee!! Plus we were traveling with my elderly parents and having a main floor bedroom and bathroom was super helpful. If we need to visit this area again, this would be the home of our choice.

4.99 out of 5 average rating, 71 reviews

Luxe Zen Retreat

CadeRating, 5 stars4 days ago

Came to stay for a wedding. Could tell the home was newly renovated and very clean. Great place to stay.

4.9 out of 5 average rating, 60 reviews

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room

DavidRating, 5 stars5 months ago

The Oasis was perfect for our needs . We will definitely book it again in the future!

4.98 out of 5 average rating, 44 reviews

Beautifully Renovated 4BR/3Bath on Riverside Dr.

MicheleRating, 5 stars1 week ago

This house was very clean and comfortable. My family stayed here for my brother’s wedding and it did not disappoint!

4.93 out of 5 average rating, 15 reviews

Home in Princess Anne

countryside home in Princess Anne

ChristenRating, 5 stars1 day ago

10 stars – The Best Host & Perfect Stay! This country spot was everything we needed and more! Super clean, incredibly peaceful, and the perfect escape from the noise of everyday life. The best surprise? Not a single mosquito in sight—which is rare for the country! The host was amazing and made the whole experience even better. We even extended our stay because we didn't want to leave. Already planning our next visit. Highly recommend!