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Vacation rentals in Toddville

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Top-rated vacation rentals in Toddville

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

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Top guest favorite
The exterior of the house is depicted, featuring a white clapboard façade. Large windows provide natural light, and a small front porch is visible. A yard with well-maintained green grass surrounds the home, offering ample space for outdoor activities.
Home in Church Creek
4.81 out of 5 average rating, 100 reviews

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.

Guest favorite
Home in Lexington Park
4.93 out of 5 average rating, 104 reviews

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.

Guest favorite
A bright kitchen area is featured, highlighting a round table surrounded by four white chairs. Natural light streams in through the sliding glass door, which overlooks greenery. Modern cabinetry and stainless steel appliances are visible, creating a functional and welcoming space.
Home in Tyaskin
4.93 out of 5 average rating, 40 reviews

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.

Guest favorite
A serene waterfront view is presented, featuring a wooden dock extending over still water. Lush green grass fills the foreground, while trees line the opposite bank, creating a natural backdrop under a partly cloudy blue sky.
Home in Woolford
4.93 out of 5 average rating, 194 reviews

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!

Top guest favorite
A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.
Home in Dameron
4.99 out of 5 average rating, 142 reviews

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.

Guest favorite
The two-story farmhouse is surrounded by a spacious yard, highlighted by a prominent American flag flying in front. Large windows allow natural light, while the earthy green exterior blends with the surrounding trees. A charming white bench adds to the inviting outdoor space.
Home in Deal Island
4.94 out of 5 average rating, 51 reviews

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!

Guest favorite
An outdoor seating area is surrounded by lush green grass, featuring a circular table and benches made of stone. A vibrant sunset casts warm hues across the sky, with trees standing tall in the background and the water's edge visible in the distance.
Home in Fishing Creek
4.88 out of 5 average rating, 17 reviews

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.

Top guest favorite
A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.
Home in Leonardtown
4.99 out of 5 average rating, 139 reviews

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”).

Top guest favorite
The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.
Home in Lusby
4.99 out of 5 average rating, 175 reviews

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).

Guest favorite
The property is framed by lush greenery with a spacious yard leading to Chesapeake Bay. A sunset casts vibrant hues over the water, while the in-ground pool and patio area are visible in the foreground, inviting relaxation and outdoor activities.
Home in Fishing Creek
4.9 out of 5 average rating, 60 reviews

BayFront Villa on Chesapeake, Newly Renovated Pool

Welcome to the beautiful Villa on Chesapeake bay. Perfect for your next family vacation with so much to do! Located bayside with fishing, crabbing and oysters from your own private dock. Lounge by our newly renovated custom pool and relax in the hot tub, make memories around the campfire and enjoy spectacular sunsets over the water. Children will enjoy our putt putt golf,swing set and gameroom! Sleeps 19 guests.

Top guest favorite
Two white Adirondack chairs are positioned on a grassy area, facing a calm water view. A stone fountain stands nearby, and a wooden dock extends into the water, offering a serene atmosphere with trees lining the shore.
Cottage in Hollywood
4.99 out of 5 average rating, 107 reviews

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". ✨

Guest favorite
Home in Fishing Creek
5.0 out of 5 average rating, 16 reviews

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!

Popular amenities for Toddville vacation rentals