Vacation rentals in Wingate

House in Sika Deer & Snakehead Country

New AT&T 5G tower just turn on! Tower just a mile away! All others very weak! The house has a pond in back of it has snakehead's in it. There is also catfish & crab in the pond too. The property has a area to fish off of the bank. If you stay in the house you are in the hart of snakehead county. Blackwater refuge is just a few minutes away. You can launch kayaks off the property. The pond is about 4 acres and by kayak you can fish whole pond. It all private property around pond just land owners.

Wits End Retreat-Relaxing Beautiful 3 Bedroom home

Leave your cares behind when you stay at Wits End. Relax with the whole family, take a couples getaway or stay long term at this peaceful property. This 1800 sq. ft. 3 bedroom 2 bathroom rancher style home has the comfort of modern amenities in a beautiful rural country-like setting. It's steps away from a community park, minutes away from several bodies of water including the Chesapeake Bay and a short drive to the Point Lookout State Park, St. Mary's College of MD and Patuxent Naval Air Base.

Serenity Bay-PrivPool-HotTub-AskAbout2NightStays!

Now offering 2-night stays!! Send a msg to ask about this! Just added-Hot Tub! Spacious, relaxing, and scenic bay-view house with canoe/kayak access to the Chesapeake Bay. We've just put in a hot tub!!! Photos will be taken when it stops raining. Six bedrooms and 5 full baths. Lots to do with an outdoor pool, an nicely equipped recreation room, and a dock from which to launch your kayak or canoe. Easy access to plenty of activities in the surrounding area makes for a memorable vacation.

Deal Island Lodge

Recently renovated 1960's farmhouse located in an authentic watermen's community. -pets allowed - with approval prior to check-in -very clean, quiet, cozy and relaxing -use of entire home -8 parking spaces -fully stocked kitchen -all linens and towels provided -screened porch with patio furniture -back deck with seating and grill -3 beach cruisers -4 beach chairs Things to do: fishing boating crabbing beach swimming kayaking and canoeing paddle boarding bird watching biking wildlife

Nature retreat with water view

Welcome to this cozy updated two bedroom, one bathroom single family home with a water view of the Nanticoke River. Enjoy the wrap around porch, with gazebo, fire pit, outdoor shower, sink and grill. Sit on the porch and feel the breeze from the river, or walk across the street to enjoy the beach or the covered pavilion. Great area for bike riding, kayaking, paddle boarding, and windsurfing. Public marina, tennis courts and additional public beaches are minutes away.

Waterfront Getaway with Dock

Bicyclist's and outdoorsman's dream! Beautiful rancher on two waterfront acres just 4 miles from Blackwater Wildlife Refuge and Harriet Tubman National Park. 10 minute drive from downtown, the Hyatt, and the Ironman starting point as well. Ironman and Eagleman races actually pass right by! Bright, sunny, and newly renovated, it's a great place to hang your hat after a day of hunting, fishing, bicycling, or triatholon-ing! Or just take a weekend to relax on the water!

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

Rusty Anchor

Escape to the Rusty Anchor, a beautifully restored 1900s farmhouse on Deal Island, MD! With 3 cozy bedrooms, it's perfect for families or friends. Just around the corner, enjoy a cozy beach, crabbing, and easy access to fishing (Redfish, Striped Bass, Flounder) and waterfowl hunting. Only a 5-minute bike ride to beaches and boat ramps. Book now and receive a link to our store to reserve add-ons or schedule special experiences for your stay!

Wonderful beachfront house

Relax with the whole family in this accommodation where tranquility is breathed. Come and enjoy the sea. The house has 2 exits to the sea to receive the sunrise and the spectacle of the sunset. It is also equipped with kayak and paddle boards. You can train in the gym while watching the sea. The house is spacious, equipped kitchen, indoor and outdoor dining room, living room, work area, board games. Parking for 4 vehicles, outdoor grill.

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).

Cottage on the Creek

The Cottage is perfectly perched alongside Cuckold Creek showcasing the beauty of Southern Maryland. Our home provides plenty of space for relaxing together with a water view everywhere you turn. Each space is set up to provide you with the comforts of home, so you can relax and enjoy being in the moment. Located in the heart of Hollywood, not too far from stores or restaurants, but still "away from it all". ✨

Hoopers Sunset

Hoopers Island Retreat! Soak in spectacular sunsets and 270° bay views at this spacious family retreat! Sleeps 15 in 5 bedrooms, features two King suites, cozy porch with outdoor dining, and indoor seating for all. Enjoy free Wi-Fi, hammocks, kids play area, kayaks & paddleboards. Direct bay access and steps from iconic Old Salty’s Restaurant & Tiki Bar. Ideal for crabbing, boating, hiking, and more!