Holiday rentals with a pool in Wicomico County

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!

Jay's Home Away From Home Delmar, Md

Bring family & friends or relax alone at this peaceful amazing home. You will love the unique layout, amenities and stylish spaciousness of this lovely townhouse, as well as the central location, close to shopping and ALL of the local beaches. The community has many other attributes as well as safe and beautiful places to walk, ride your bike and a pool. The home is close to local activities like the Civic Center, Outlet shopping, and Wedding Venues. or you can just relax on the rear patio !

Ray’s RV Retreat

Park and stay to enjoy the sounds of nature when you stay in this unique place. Enjoy BBQing while watching the kids on the playground. Playground has a swing set with slide, above ground pool, and a trampoline. BBQ is next to a gazebo to enjoy outdoor dining. While the kids rest peacefully, enjoy a s’more over the fire. Or you can choose to take a 15 minute drive to the local beach. Plenty of options. *RV in photos will not be on site. It is located exactly where you will park your own RV.*

Family Retreat - Private Pool, 4 Bedroom, Fire Pit

Family fun awaits you at The Oyster House located in the quaint town of Bivalve, MD. This stunning home will welcome you in and wrap you in with warmth! The large open spaces for group gatherings while offering quiet areas to relax and unwind. There are just so many ways to spend the day! Jump in the Pool! Gather together for a family barbeque! Relax by the firepit! Bike to the local tiki bar! Enjoy fishing, crabbing, local beaches, and breathtaking sunsets the Nanticoke River has to offer!

Tiny Little Cabin in the Woods

Enjoy this beautiful tiny cabin. Not for the claustrophobic! A perfect little getaway space for 2. Our little 12x20' cabin is surrounded by fields and the quiet sound of country sunrise. You'll wake up to rooster crows and chickens anxious to get out of their coop. In the evenings, light the firepit or enjoy a quiet nighttime swim with our duck. Our very friendly dog, Tanka (Cane Corso) and black lab, Singer may welcome you. Treats are available to share with them should they decide to visit.

Loch Raven Retreat/spacious home w/ private pool

Our spacious home allows you to enjoy a relaxing night watching a movie on the cozy sectional, cooking a big meal in the gourmet kitchen, swimming and grilling or a game night in the large family room. Walking distance to the park for a peaceful sunset. Conveniently located 10 minutes from Salisbury University and Henry Parker Sports Compex. For a day trip, we’re 30 minutes to Ocean City and Assateaque Island. Lots of local attractions too. Just bring a suitcase, we’ve got the rest covered.

Farm Cottage - POOL - 30 Min to BEACH

Enjoy this beautiful cottage/studio apartment. Perfect little getaway space for 2 (or 3). Our little cottage is surrounded by fields and the quiet sound of country sunrise. You'll wake up to chickens anxious to get out of their coop or Lucy, the turkey, peeking in your window. In the evenings, light the firepit or enjoy and a quiet nighttime swim with our duck. And our very friendly dog, Tanka (Cane Corso) will welcome you to our family.

Modern Coastal Vacation Home: pool, beach, golfing

Welcome to our spacious, modern coastal-styled home in Delmar, Maryland. Quiet settings located in the heart of the Eastern Shore close to several beaches, wedding venues such as Kylan Barn, The Southern Belle & many restaurants/shops. Neighboring Ocean City and Rehoboth Beach, enjoy a quiet getaway in this beautiful, newly renovated 3-bedroom house.

Kits Cottage on "Just Ducky Acres"

Escape to Kits Cottage, a serene haven on 6 acres at Just Ducky Acres. Unplug and unwind in the peaceful atmosphere, surrounded by friendly farm animals. Perfect for romantic getaways, family retreats, or solo escapes. Relax, reflect, and reconnect in this idyllic setting, just a short drive from Ocean City and other area attractions.

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

Escape to this stylish 4BR 2.5BA retreat featuring a full game room, private movie theater, and a stunning backyard oasis with pool. Perfectly located near beaches, restaurants, and shops—ideal for both relaxation and adventure. Whether you're lounging poolside or enjoying a movie night in, this spacious home is the perfect getaway!

New Coastal Style Vacation Home

Bring the whole family to this great place with lots of room for fun.