
Holiday houses in Calvert Cliffs
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Top-rated holiday rentals in Calvert Cliffs
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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.

Historic St.Mary's City at the Lazy Bear Cottage
Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

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.

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.

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.

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🥰

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!

Serene setting great location surrounded by woods
The one-bedroom apartment will sleep 2 adults and 1 child under 18. In a serene setting with woods, a fish pond, and a comfortable patio. Separate code lock entrance. Well-equipped kitchen. Free WiFi, two TVs with Netflix and Amazon Prime. There is also a cedar sauna. Parking is on the property. Apartment situated near shops, restaurants, St. Mary's College and the Patuxent River Naval Air Station. 15 minutes from Chesapeake Bay, 1 hour to DC beltway. French and German also spoken.

Chic Loft Retreat | Private Beach & Near Solomons
STAY IN or ADVENTURE OUT Relax in a chic, private loft just 5 minutes from Chesapeake beaches and 10 minutes from Solomons & Calvert Cliffs. Enjoy your own 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.

Adorable Waterfront Apartment Weekend Getaway
Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

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.

“Cabana by the Bay”-tiny home on a pier!
This tiny home is a newly renovated cabana sitting on a pier. Fall asleep to the sound of waves crashing under you! Enjoy shared use of our private beach. Bikes are available April-October and are stored directly across the street. Go crabbing or fishing off the pier and walk to one of the many nearby restaurants. Check out the summer concert series at the Calvert Marine Museum.
Popular amenities for Calvert Cliffs holiday rentals
Other great holiday rentals in Calvert Cliffs

Air BnB available for single professional.

The Path

HJLL Magnolia Farm Apt 2

Peninsula Pad

The Hideaway. Towering Trees. Privacy. Studio Apt.

Camelot Cottage

The Osprey Nest

Yorktown Rd
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- Nationals Park
- The White House
- National Mall
- District Wharf
- Smithsonian National Museum of Natural History
- National Museum of African American History and Culture
- Sandy Point State Park
- Arlington National Cemetery
- Georgetown Waterfront Park
- National Harbor
- Washington Monument
- Six Flags America
- The Pentagon
- Smithsonian American Art Museum
- Library of Congress
- Lincoln Park
- Piney Point Beach
- Quiet Waters Park
- Breezy Point Beach & Campground
- American African Museum
- Meridian Hill Park
- Ragged Point Beach
- Chesapeake Beach Water Park
- Heritage Shores