Vacation rentals in Chesapeake Ranch Estates-Drum Point

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Top-rated vacation rentals in Chesapeake Ranch Estates-Drum Point

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Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 310 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 completely 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 beautiful Solomon’s island. Boaters welcome!

Guest favorite

Apartment in California

4.91 out of 5 average rating, 187 reviews

Our Little Piece of Heaven

Our cozy studio apartment sets on the Patuxent River. With the perfect views of Myrtle Beach, Point Patient and Thomas Johnson Bridge. Relax watching the boats and birds or take a walk along the water for a lovely neighborhood to stroll for 2.5 miles. Your favorite moments may be when you wake to see the sun rise and again to see the orange sky set. Just over the bridge from the popular Solomon's Island which is full of fabulous restaurants, boat rentals, charter fishing and summer concerts.

Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 167 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

Cottage in California

4.97 out of 5 average rating, 198 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan 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 and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

Guest favorite

Cabin in Lusby

4.91 out of 5 average rating, 215 reviews

Peaceful Waterfront Retreat on The Bay

This is a serene, waterside cabin with a private dock, nestled on quiet St. Leonard Creek about one hour outside of Washington, DC. You will enjoy a close quarters stay in this rustic studio cabin, and it is the perfect getaway for anyone looking for some peace and quiet. Come on your own to finally get some work done, or bring your family to enjoy the outdoors! We have two kayaks and two canoes. The house is great for up to two couples looking to catch up and explore the surrounding area.

Guest favorite

Apartment in Lexington Park

4.97 out of 5 average rating, 107 reviews

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.

Guest favorite

Loft in Lusby

5.0 out of 5 average rating, 321 reviews

Coastal Treetop Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction stove, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 322 reviews

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!

Guest favorite

Home in Lusby

4.99 out of 5 average rating, 180 reviews

Cove Point Cottage with Chesapeake Bay views

Cozy beach house just one block from the sandy Cove Point Beach on the Chesapeake Bay. Grab the beach wagon from the shed, load up with beach chairs, towels and your cooler and take a short stroll to enjoy a day at the beach searching for sharks teeth, shells and swimming in the bay. Rinse off in our outdoor shower and enjoy a relaxing evening by the fireplace, reading in the sunroom overlooking the bay or on the outdoor shady patio

Guest favorite

Apartment in Solomons

4.99 out of 5 average rating, 237 reviews

Island Breeze Solomons

Cute studio apartment on charming Solomons Island. Walking distance to restaurants, live music, boat and kayak rentals. The kitchen has a full sized refrigerator, microwave, toaster, two burner hot plate and coffee maker. We provide all bedding and bath towels for two people. Enjoy your coffee ( provided) or wine on the deck in the fenced in side yard. One well-behaved pet is welcome. Please make sure you pay the pet fee.

Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 550 reviews

“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.

Guest favorite

Home in Lusby

5.0 out of 5 average rating, 114 reviews

Historic Rousby Hall, Waterfront, Patuxent River

Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300-foot private beach. The year-round property has a pier, and in-ground pool (May-October) with amazing river views.