Vacation rentals in Chesapeake Ranch Estates-Drum Point

4.92 out of 5 average rating, 215 reviews

Apartment in California

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.

4.93 out of 5 average rating, 203 reviews

An outdoor fire pit is surrounded by several black adirondack chairs, creating a cozy gathering space. The scene is set against a backdrop of lush trees and St. Leonard's Creek, with dusk settling in and a soft blue hue filling the sky.

Cabin in Lusby

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 --

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 348 reviews

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.

5 out of 5 average rating, 371 reviews

A wooden dock extends over the water, leading to a sun setting on the horizon. Waves gently lap against the sides, reflecting warm hues of orange and pink as the sky transitions into dusk. Two benches are positioned on the dock, inviting peaceful contemplation.

Loft in Lusby

Treetop Loft Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private above-garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction burner, 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.

A sandy beach extends along the shore, meeting the calm waters under a pastel sky. A lighthouse stands tall in the distance, accompanied by a house with a red roof. The shoreline appears tranquil, with gentle waves lapping at the sand.

4.99 out of 5 average rating, 212 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.

4.98 out of 5 average rating, 347 reviews

A cozy bedroom features a wooden bed adorned with soft linens and decorative pillows. Warm string lights drape along the sloped ceiling, creating a gentle glow. Framed artwork and bedside lamps add character to the space, while the walls exhibit a calming blue hue.

Guest suite in Lusby

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🥰

Apartment in Lexington Park

An aerial view showcases a blend of natural landscapes and developed areas, featuring a winding road alongside greenery and water. Structures near the shoreline include buildings and marina facilities, with boats anchored in the harbor, surrounded by trees and fields.

4.97 out of 5 average rating, 130 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.

A coffee station is displayed on a sleek white countertop, featuring a coffee machine and a clear container filled with various coffee pods. An inspirational sign is mounted on the wall, adding a welcoming touch to the space.

4.96 out of 5 average rating, 144 reviews

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Coastal Oasis On The Chesapeake is where you come to: RELAX, DECOMPRESS and RE-CHARGE! You'll experience all the tranquility & majestic beauty of PEACEFUL living on the Chesapeake Bay. You'll awaken to breathtaking & alluring sunrises while also being surrounded by nature's wooded bliss of starry nights. Located 4 miles from Solomon's Island. Contact host for pre-approval of pets, pet fee applies. Unregistered: guests/pets & smoking including marijuana will incur fines!

A lighthouse rises against a colorful sunset, with vibrant clouds reflected in the water. The sandy beach curves alongside the rocky shoreline, while the quaint white structure with red accents stands prominently, showcasing a serene coastal scene.

5 out of 5 average rating, 184 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.

4.97 out of 5 average rating, 235 reviews

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

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.

4.99 out of 5 average rating, 289 reviews

A wooden staircase leads up to a sign reading 'Island Breeze,' mounted on a railing. The entrance is bordered by a low brick wall and features greenery, including a potted plant. A lamp post stands nearby, illuminating the area.

Apartment in Solomons

Walk to famous Tiki Bar on Solomons Island!

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.

5 out of 5 average rating, 140 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

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. Also hosts weddings+events up to 100 guests.

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Popular amenities for Chesapeake Ranch Estates-Drum Point vacation rentals

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Pool

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Other great vacation rentals in Chesapeake Ranch Estates-Drum Point

4.72 out of 5 average rating, 211 reviews

A classic lighthouse stands on rugged rocks, illuminated by the warm glow of the setting sun. The surrounding landscape features scattered trees and distant islands, while the serene waters extend beyond the rocky shore, reflecting the calming colors of twilight.

Apartment in Lusby

Nice view self-contained Apart.

MargaretRating, 5 stars1 month ago

I really enjoy staying here at nice view. very peaceful and close to work. has everything I need and very comfortable bed. always responsive when I had a question. would definitely stay here again.

Superhost

4.75 out of 5 average rating, 4 reviews

Bear Hollow

JoseRating, 5 stars2 months ago

We had an incredible stay, exceeded our expectations, and we can’t wait to return! Highly recommend it for anyone looking for a peaceful escape.

5 out of 5 average rating, 6 reviews

Driftwood Haven, Chesapeake Bay views throughout

MicaelaRating, 5 stars5 days ago

This was one of the best Airbnbs I’ve ever stayed at. It was beautiful, clean, and felt like home. My only complaint was the lack of blinds. There was work being done next door and the workers could see into the house (or it felt like they could). There was also a worker there at 9:30 PM one of the nights who could definitely see in and it was a bit creepy haha. I would definitely recommend the Airbnb regardless and we would love to come back again in the future! Sylvia also was very quick to respond to us and she did warn us about the work being done on the neighboring house the one day which was nice to know! Five stars for sure!!

5 out of 5 average rating, 5 reviews

A modern bathroom features three round mirrors above a double sink vanity with brushed metal faucets. The space incorporates navy blue cabinetry and light-colored stone countertops. A separate shower area is visible, with a textured wall and wooden bench, on the right side of the image.

Boat in Kinsale

Spend the Night on the River

QuinnRating, 5 stars5 days ago

Unique experience to stay on a boat! We had a lovely night on the boat at The Slips Marina! Annie is super kind and it's clear that they have created a community atmosphere at The Slips. They invited us to a birthday party being held at the bar and there was a taco truck for the party for dinner. The market up the street is very cute. The boat itself is very nicely appointed with a rather large bed in the bow, comfy linens, snacks, and everything you need. I felt like we were glamping on a boat, but with nice bathrooms a short walk (30 sec) away. We swam in the pool, played table tennis, and relaxed.

4.97 out of 5 average rating, 32 reviews

A neatly arranged living room features a comfortable gray sofa adorned with decorative cushions. A flat-screen TV is mounted on the wall above a modern white media cabinet. A wooden coffee table with decorative items sits on a soft area rug, and stylish lamps illuminate the space.

Apartment in Great Mills

Furnished Corporate Apartment Near NAS Pax

KelleyRating, 5 stars2 weeks ago

Really nice fully furnished basement with private entrance and a kitchen. The place was dog friendly and even had a small fenced in back yard that was great to let our dog walk around and get some exercise. Very spacious basement with washer and dryer. The hosts were very quick to respond to any questions.

4.98 out of 5 average rating, 90 reviews

A wooden path leads to a private pier by the lake, surrounded by greenery. A fire pit with seating for eight is situated nearby, providing a cozy gathering spot, while kayaks are visible at the water's edge, ready for use.

Cabin in Lusby

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

LaurenRating, 5 stars1 week ago

We stayed at Julie’s home with a group of friends and our families and had a wonderful time. The lakefront setting was incredibly relaxing—we found ourselves rarely leaving the property because it had everything we needed. From soaking in the hot tub to enjoying the game room, there was something for everyone. The kids loved having space to run around in the basement, while the adults enjoyed peaceful mornings and evenings on the screened-in porch. Julie was very responsive and answered all of our questions quickly, which made the entire experience seamless. We would absolutely stay here again!

4.99 out of 5 average rating, 80 reviews

An outdoor deck is presented, featuring a cozy seating arrangement with a gas fireplace. A view of the water is visible, framed by large windows and trees. Warm hues from the sunset illuminate the scene, creating a serene atmosphere with Adirondack chairs in the background.

Home in Leonardtown

Water's Edge Cottage | Luxury Retreat

BenjaminRating, 5 stars2 weeks ago

Incredibly peaceful, beautiful spot. The interior was so nicely set up—it really allowed us to enjoy the gorgeous views of the river. Kitchen is very well appointed, we didn’t have to go anywhere. Great, quiet area, enjoyed the tranquil evenings.

Superhost

Two turquoise adirondack chairs are positioned on a wooden dock, overlooking a calm body of water. Lush, wooded land frames the view across the water, and a clear blue sky with wispy clouds is visible above.