Holiday rentals with outdoor seating in Chesapeak Ranch Estates

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Top-rated Holiday Houses with Outdoor Seating in Chesapeak Ranch Estates

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Top Guest favourite
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, 220 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 favourite
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, 253 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 favourite
A bright living area is illuminated by large windows, providing a view of the surrounding greenery. A comfortable sectional sofa is arranged around a centerpiece coffee table, while a small pool table sits nearby. Natural light enhances the airy atmosphere of the room.
Home in Lusby
4.9 out of 5 average rating, 115 reviews

SoMD Waffle House 1.5 acres of cozy coastal living

Welcome to our Southern MD beach house. This 3 bedroom and 2 bath home is situated on nearly 1.5 acres of property where you can breathe deep and take in the bay breeze. Whether it is visiting one of the Chesapeake Bay beaches only a 3 minute drive from the home, or watching for wildlife in our yard (it is common to see deer, rabbits, birds, etc), life in Calvert County will slow you down and help you take a much needed break from the daily grind. And you don't even have to cross the Bay Bridge!

Guest favourite
Four black Adirondack chairs are arranged on a lush green lawn, facing the calm waters of Chesapeake Bay. Gentle waves reflect the bright blue sky, offering a serene view. Small bushes line the edge of the property, providing a natural border.
Home in Lusby
4.98 out of 5 average rating, 103 reviews

Waterfront with sweeping bay view & private beach

Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

Top Guest favourite
The charming beach house features a white picket fence and a welcoming front porch. A large anchor motif is displayed prominently above the door. Surrounding greenery provides a natural backdrop, enhancing the cozy exterior aesthetics in a tranquil setting.
Cottage in Lusby
4.98 out of 5 average rating, 298 reviews

Gettin to the point. ( Cove Point Beach)

Our beach house is for you to enjoy Cove Point Beach, which is only 500 ft away. The kitchen is fully stocked, or use the outdoor grill on the side of the house.PLEASE NON SMOKERS ONLY. One dog allowed on a cases by case bases with a one time pet fee of $65.00. No children under 8 years old. Walk to the beach, but only park your vehicle in our driveway, not on beach inlets. A gas fireplace in the living room. A beautiful sun porch area to enjoy. Enjoy walking on this private community beach.

Top Guest favourite
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, 132 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 favourite
The exterior of a single-story beach house is visible, featuring white siding and landscaped areas. A stone pathway leads to a cozy outdoor seating area with light cushions. Lush greenery and mature trees are present, contributing to a serene atmosphere.
Home in Lusby
4.98 out of 5 average rating, 245 reviews

Cove Point Cottage with Chesapeake Bay views

Welcome to our beach house, just a block from the Cove Point Beach on the Chesapeake Bay. Start your beach day by grabbing the beach wagon from the shed, loading it up with beach chairs, towels, and your cooler. A short stroll takes you to the beach, where you can spend the day searching for shark teeth and shells or swimming in the bay's refreshing waters. After a day in the sun, rinse off in our outdoor shower. Our shady patio provides the perfect spot to relax and enjoy the evening breeze.

Top Guest favourite
The exterior of a two-story house is showcased, featuring light blue siding and white railings. A grassy area is visible in front, with four gray Adirondack chairs arranged around a circular fire pit on a stone patio. The sun casts a warm glow over the scene.
Home in Solomons
5 out of 5 average rating, 129 reviews

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

Top Guest favourite
A stone pathway leads to a two-story house with white siding and turquoise accents. A fenced yard features a well-maintained lawn. The entrance is adorned with a porch that includes two chairs, providing a welcoming space for relaxation. Overhead, the sky presents a mix of clouds.
Home in Solomons
4.89 out of 5 average rating, 154 reviews

Perfect spot for a Vacay!

Be an Islander! This incredibly well-positioned home has 6-car parking and views of the Patuxent River and Solomons Island. Enjoy year-round life on the water. This is the dream vacation spot with so much to offer. Watch fireworks, fish, crab, enjoy beautiful sunrises & sunsets from the private pier or while relaxing in the gazebo. The local marina, shops, bars, and restaurants are within walking distance. Enjoy the best seafood Southern Maryland has to offer, a crab cake to die for!

Top Guest favourite
The kitchen area features a light grey cabinetry with wooden countertops. A vintage-style turquoise refrigerator stands beside a stylish coffee station, complete with a microwave. Decorative items and plants are arranged on the shelves, adding functional charm to the compact space.
Houseboat in Solomons
5 out of 5 average rating, 119 reviews

Island Shanty

Cozy custom built houseboats on charming Solomons Island. Walking distance to restaurants, live music, boardwalk and unique shops. In the morning, have your coffee on the deck overlooking the harbor and watch the sailboats going by. In the evening enjoy a glass of wine on the deck while you listen to good bands on the weekends at the famous Tiki Bar. One SMALL well behaved pet ( no barkers please) is allowed and must be approved by owner $100 non- refundable pet fee.

Top Guest favourite
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, 410 reviews

Relaxing Beach Getaway Loft near Solomons

Note: We are a peanut-free property. RELAX in our chic, private loft just 5 minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach just a five minute drive away. Enjoy our private, above-garage hideaway apartment with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance. Come and go as you please!

Top Guest favourite
A welcoming cottage exterior features a covered porch with seating, light fixtures, and colorful plantings. A walkway made of stone leads to the entrance, and the surrounding landscape is highlighted by well-maintained grass and nearby neighboring homes.
Cottage in California
4.97 out of 5 average rating, 272 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum featuring live concerts by top name bands.

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