Cabin holiday rentals in Southern Maryland

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Top-rated cabin rentals in Southern Maryland

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Superhost

Cabin in Richardsville

4.85 out of 5 average rating, 130 reviews

NEW Cabin in the Woods🏕

Sit on the porch and enjoy your remote cabin getaway with plenty of solitude on thirteen acres of spacious, wooded, serenity. The birds are chirping and wildlife is in the woods. My cabin is a one-of-a-kind experience to share with close friends and family. The cabin is an A-framed loft style dwelling made from pine milled saddle-notch logs. There is plenty of outdoor space which includes front and covered side porches, pasture, a fire pit and hammock for relaxation that you'll be sure to enjoy!

Guest favourite

Cabin in Lusby

4.93 out of 5 average rating, 205 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

Cabin in Lusby

4.98 out of 5 average rating, 90 reviews

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Welcome to The Lake House - our freshly updated 3 bedroom, 3 bath cabin on Lake Vista with views of the Patuxent River/Chesapeake Bay from the private pier. Enjoy everything Southern Maryland has to offer all within a 10 minute drive - Calvert Cliffs, Flag Ponds, Solomons Island - hiking, fishing, boating and beaches. Located just 90 minutes outside DC, The Lake House will become your new go-to retreat from the hustle. Come relax and make memories on the water with your family and friends.

Superhost

Cabin in Lusby

4.9 out of 5 average rating, 10 reviews

COZY BLACK LoG HoUSe

Nestled in a quiet country setting our home offers quick access to state parks and beaches, desirable Solomon's Island, and a retreat from the world. Guests can expect a welcoming stay with all your essentials for a long or short term visit plus extra touches to make your experience memorable. What do guests love most about our home? Guests love our country setting - life slows down and the rush of our daily lives slips away. Our space is designed for a relaxing and no-stress get-away.

Top guest favourite

Cabin in Spotsylvania Courthouse

4.97 out of 5 average rating, 435 reviews

The Tobacco Barn

A high-peaked ceiling and exposed-log crossbeams reveal the Tobacco Barn’s past life as a place for hanging tobacco leaves to dry. Now converted to a one-room guest house, it features a front porch swing, cozy fireplace, soapstone floors, a homey sitting area, and a tall, high-post bed. The pressed-tin ceiling and whiskey-barrel sink in the bathroom add to its charm. Pets are allowed and are charged a fee of $25 (first night) and $15 (per ea. add'l night). Maximum two-person occupancy.

Guest favourite

Cabin in Ridge

4.95 out of 5 average rating, 65 reviews

Pizza Friday

Magnificent 26-acre waterfront property just off the Potomac River. This secluded, quiet waterfront oasis boasts four-bedroom and two-full baths with large picture windows offering panoramic water views from almost every room. The large updated kitchen features stainless appliances, ample cabinetry, granite countertops, and a breakfast nook. There is a large sunny dock, a pizza oven, kayaks and a canoe to enjoy the water. If you're looking for the perfect weekend getaway, this is it!

Guest favourite

Cabin in Colonial Beach

4.96 out of 5 average rating, 156 reviews

Summer Perfect, Water Front A-frame on Winery

This serene cabin is on the Ingleside Vineyard's property. Have a glass or two of wine and walk around the vineyards and then retreat to your own private a-frame cabin oasis. A beautiful view of the Roxsbury Estate where abundant wildlife can be viewed all around the property and the pond is stocked and ready to be fished. Within driving distance to wineries, Stratford Hall, George Washington & James Monroe's birthplace, Westmoreland State Park, and the beach town of Colonial Beach.

Superhost

Cabin in Lusby

4.78 out of 5 average rating, 23 reviews

Covenant Cove (Cove Point Beach)

Nestled at the edge of the Chesapeake Bay, next to the iconic Cove Point Lighthouse, this charming cabin offers a peaceful and rustic escape from the everyday hustle and bustle. Situated in the serene surroundings of Cove Point, the cabin provides a perfect blend of comfort and simplicity, ideal for those seeking a quiet retreat amidst nature. One of the main highlights of staying at this cabin is its proximity to the private community beach, located just a short walk away.

Top guest favourite

Cabin in Lusby

4.99 out of 5 average rating, 87 reviews

Beachfront Escape with Horizon Views of the Bay

Modern beachfront Panabode log cabin with sweeping Chesapeake Bay views. Relax on the deck, in the hot tub, swing, beach, or by the fire pit. Enjoy kayaks, paddleboards, shallow water, landscaping, and wildlife sightings. Main bedroom has king bed and ensuite bath. No pets, visitors, or street parking. Guests must bring linens, towels, and remove trash. Peaceful beachfront escape with modern, rustic charm, and unforgettable views.

Guest favourite

Cabin in Reedville

4.97 out of 5 average rating, 261 reviews

Dinna Fash-3 BR Waterfront Log Cabin

Welcome to “Dinna Fash,” our cozy waterfront cabin on the Little Wicomico River. Whether you need a change of scenery while working virtually with our high speed internet and fully equipped kitchen, or just some R & R, “Dinna Fash” is it! Bring your kayaks and paddle boards to explore the beautiful waterway that opens up to the Chesapeake Bay. Watch the boats troll by from our natural rock fire pit and comfy Adirondack chairs.

Guest favourite

Cabin in Lusby

4.9 out of 5 average rating, 268 reviews

Peaceful Waterfront Retreat on The Bay

Escape to a serene waterside cabin with a private dock on quiet St. Leonard Creek, just an hour from Washington, DC. This rustic studio offers a cozy retreat for solo travelers, couples, or small families looking for peace and relaxation. Whether you're here to unwind, work remotely, or explore the outdoors, you'll find plenty to enjoy—including two kayaks, two canoes, and stunning waterfront views.

Guest favourite

Cabin in Saint Michaels

4.99 out of 5 average rating, 112 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

TREMEZZO STAY - Spencer Creek Cabin Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD. If you do not see availability for your dates or are looking to sleep more than 8 please visit our additional exclusive listings! Punch Point (sleeps 10) Chesapeake Mansion (sleeps 12) Ranch at Royal Oak (sleeps 12)