Vacation rentals in Taylors Island

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Top-rated vacation rentals in Taylors Island

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Top guest favorite
A spacious living area features a comfortable sofa adorned with decorative pillows. A dining area with wooden chairs is visible, alongside a kitchenette equipped with appliances. Natural light floods the room through large glass doors, while decorative blue and white accents enhance the atmosphere.
Farm stay in Madison
4.98 out of 5 average rating, 210 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Guest favorite
The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.
Cabin in Lusby
4.91 out of 5 average rating, 232 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Top guest favorite
A bright dining area features a wooden table surrounded by four chairs, illuminated by natural light from the sliding glass doors. A cozy armchair with a soft throw blanket is present, with a clock and decorative art pieces on the walls, creating a welcoming atmosphere.
Apartment in Church Creek
4.97 out of 5 average rating, 430 reviews

Nature's Rest in Church Creek

Nature's Rest is located just minutes from Blackwater Wildlife Refuge, The Harriet Tubman Museum, Blackwater Adventures! Boat ramps are close by for easy access to the Chesapeake Bay and its tributaries for enjoying Maryland's Eastern Shore. We have plenty of parking, so bring your boat, bikes, and binoculars. Just mins from downtown Cambridge for dining & shopping. Discover the many quaint towns the area has to offer, come for a night, or stay as long as you'd like, look forward to meeting you.

Top guest favorite
A collection of various fossilized shark teeth is displayed on an orange background. The teeth are of different sizes and shapes, showcasing both small and large specimens, with some exhibiting intricate details. The vibrant color of the background contrasts with the dark tones of the teeth.
Home in Lusby
4.95 out of 5 average rating, 122 reviews

Soul Oasis - home on the Chesapeake Bay

Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

Top guest favorite
A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.
Home in Cambridge
4.99 out of 5 average rating, 189 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

Top guest favorite
Two light blue Adirondack chairs are positioned on a wooden dock, facing a calm river. The sun sets over the water, casting a warm glow across the surface and creating a serene atmosphere. A weathered wooden table is placed nearby, enhancing the inviting scene.
Guest suite in Lusby
4.98 out of 5 average rating, 364 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

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, 107 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”). And be sure to visit our sister property, White Point Cottage!

Top guest favorite
A peaceful sleeping area features a neatly made bed with floral-patterned bedding in blue tones. A wooden nightstand holds a book and a small plant, while a warm light illuminates the wall, creating a cozy ambiance.
Loft in Lusby
5 out of 5 average rating, 394 reviews

Chic Loft | Rest and Relax Near Solomon's & Beach

STAY IN or ADVENTURE OUT Relax in a chic, private loft just 5 minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. Enjoy our private, above-garage hideaway with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. Our open-concept space, has a bedroom area, bathroom, workspace, living room & kitchen. SMOKE FREE SCENT FREE PET FREE PEANUT FREE We offer an Air Purifier and use only all natural cleaning products.

Top 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, 168 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
The exterior of a renovated beach house is depicted, featuring a wide entrance with steps leading to a spacious deck. The deck is furnished with a dining set and a shaded lounge area, while greenery surrounds the property, enhancing its tranquil setting.
Home in Lusby
5 out of 5 average rating, 211 reviews

Cove Point Beach Home 1 &1/2 blocks to Beach

"Welcome to our Beach House, located in the unique peaceful private beach community of Cove Point. You'll enjoy the tranquility and the beauty of living less than a 2 min walk to the sandy beach and just a few away from Solomon's Island, MD. Our home was just renovated and is ready for your family to enjoy, offering beach necessities (wagon, chairs, umbrella, & toys) and recreational equipment (bikes & kayaks). This will be your home away from home.

Guest favorite
A historical lighthouse and keeper's home are situated on a grassy expanse, with the coastal water visible in the background. The lighthouse features a white tower topped with a black lantern, while the two-story white cottage includes a welcoming porch and large windows.
Lighthouse in Lusby
4.97 out of 5 average rating, 113 reviews

Cove Point Lighthouse Keeper's House- Side B

UPDATE: CPLH Reservations are paused until August 12th. Please check back for future dates! Listed on the National Register of Historic Places and cared for by the Calvert Marine Museum (CMM), the Cove Point Lighthouse historic site has been lovingly restored and re-purposed so that it can be enjoyed by all. The active lighthouse and keeper's home sit on a seven-acre point of land in one of the narrowest points of the Chesapeake Bay.

Top guest favorite
A charming single-story house is framed by vibrant pink flowering trees. The facade features yellow siding, blue shutters, and a turquoise front door. A white picket fence encloses the front yard, which is well-maintained with green grass and landscaping.
Home in North Beach
4.97 out of 5 average rating, 167 reviews

Beach Home | King Bds | Firepit | Backyard Dining

Welcome to A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor.

Popular amenities for Taylors Island vacation rentals