Cottage holiday rentals in Southern Maryland

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Top-rated cottage rentals in Southern Maryland

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Guest favourite

Cottage

4.98 out of 5 average rating, 268 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.

Guest favourite

Cottage

4.96 out of 5 average rating, 167 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Guest favourite

Cottage

4.96 out of 5 average rating, 139 reviews

River view dog friendly YOLO Beach House

YOLO Beach House has a gorgeous sunrise view only one block to the river & blocks to the beach. Fenced yard excellent for children & dogs (dog door to back yard). Recently updated. Walking distance to Dockside, Castlewood park & the boat landing. Beach is pet friendly Oct to Mar only. The house & property are no smoking. Home has a whole home backup generator that does a self-check on Monday morning. It will start automatically if power is lost. We hope you enjoy YOLO as much as we do!

Guest favourite

Cottage

4.91 out of 5 average rating, 102 reviews

Waterfront Cottage w Hot Tub, Kayak, Fishing

Come relax in our delightful waterfront home decorated with classic cottage décor. Sit out on one of the two big screened-in porches, go for a swim in the shallow brackish (mostly fresh) water, take a dip in the hot tub, or throw one of our crab pots in the water and enjoy the spoils of the waters off the Potomac River. Our house is situated off the Potomac on Hull Creek, which means the water is nice and shallow for little ones to play, and there are plenty of crabs to be caught!

Guest favourite

Cottage

4.97 out of 5 average rating, 158 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Superhost

Cottage

4.94 out of 5 average rating, 108 reviews

Modern 2 Bdrm Cottage in Historic River Community

Remodeled river cottage available in historic, quaint Sharps. Explore this old fishing village by land or water, and enjoy perusing local artwork and farm stands. Framed by a marsh/old marina, open fields, and the Rappahanock River across the street, this unique property is just the getaway you’ve been looking for! Bicycles and paddle boards on site. Escape to a slower pace, picturesque views, and birder’s paradise, watch the osprey and eagles sail past!

Guest favourite

Cottage

4.97 out of 5 average rating, 222 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.

Guest favourite

Cottage

5 out of 5 average rating, 126 reviews

Potomac River cheerful cottage

Embark on a journey to the serenity of nature and the gentle lullaby of the Potomac River at the cottage. Escape the hustle and let the timeless embrace of water and tranquility rejuvenate your mind and soul. The private sandy beach (no public access) is steps away and awaits your footprints. Delight in the serene surroundings of the Northern Neck countryside. Two hours from DC, Richmond and Maryland.

Guest favourite

Cottage

4.98 out of 5 average rating, 137 reviews

Newly Renovated 2BR Waterfront Cottage with Dock

Escape to Mallard Cottage, our newly renovated home nestled along the picturesque Nomini Creek. Step onto the private dock for direct water access, where you can launch one of our paddleboards or kayaks for a day of exploration. Highlights include: ✔ 4 Outdoor Decks ✔ High-Speed Wi-Fi ✔ Central Heating & Air Conditioning ✔ Game Room ✔ Free Parking ✔ No Cleaning Fee

Guest favourite

Cottage

4.96 out of 5 average rating, 303 reviews

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

Guest favourite

Cottage

4.88 out of 5 average rating, 109 reviews

Spacious Beachfront Retreat w/Dock

Relax with the whole family at this peaceful place to stay. This charming home features 5 bedrooms and 3 full bathrooms. All bedrooms have a waterfront view. Enjoy watersports - kayaking, fishing, paddle boarding; or relax on the beach by a fire and enjoy the sunset. Bring your jet skis or fishing boat, the marina is 5 miles away.

Superhost

Cottage

4.9 out of 5 average rating, 102 reviews

Charming Waterfront Home with Expansive Views

Mom and Pop's Honest Point Home has been in our family for almost 70 years. It has been and continues to be a haven for anyone seeking a relaxing rural property. The cottage is situated on 25 acres surrounded by water and wildlife. Your only neighbor is the owner's home which is next door. Make sure you read the details below