House vacation rentals in Southern Maryland

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Top-rated house rentals in Southern Maryland

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Guest favorite

Home in Colonial Beach

4.97 out of 5 average rating, 116 reviews

Sunnyside Up - Dog Friendly Waterfront Cottage

Our classic cottage has beautiful expansive views of the Potomac River. Wake up to stunning sunrises & enjoy coffee in our screened front porch, or sit & relax on our own private pier. Our home is equipped with comfortable linens, a fully stocked kitchen, Smart TV, Wi-Fi, & a secluded outdoor dining area with a gas grill, fire pit & fenced yard. We are just blocks away from the public beach, downtown shops, boardwalk, and restaurants. Golf cart rentals can be reserved thru local companies

Guest favorite

Home in North Beach

5 out of 5 average rating, 124 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton, Bikes

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

Guest favorite

Home in Lusby

4.99 out of 5 average rating, 203 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.

Guest favorite

Home in Reedville

4.96 out of 5 average rating, 142 reviews

Sunkissed Cottage-private, natural waterfront home

Want a cozy, private getaway surrounded by nature, lush trees, beautiful sunsets on the Little Wicomico? Sunkissed Cottage is cheerful home full of wonderful amenities! Enjoy drinking coffee on the porch watching the deer and birds. Take a 2 minute walk down our path through the woods to our waterfront where you can enjoy the water. Our home has high speed internet, smart tvs in every bedroom, corn hole boards, firepit and gas grill. The kitchen is well stocked for all your culinary needs.

Guest favorite

Home in Montross

4.99 out of 5 average rating, 143 reviews

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

Guest favorite

Home in Leonardtown

5 out of 5 average rating, 107 reviews

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

Guest favorite

Home in Montross

4.94 out of 5 average rating, 190 reviews

The Glebe

This 3br 2ba home with own private beach is nestled off of the Potomac River and boasts serene and expansive views. Sunbathe on the private beach, cool off in the water, go fishing/crabbing from the dock, or just listen to the waves crash. Whatever it is, you’ll find it absolutely relaxing. Be sure to explore local wineries, breweries, shops and enjoy the community pool and tennis court. It's the perfect getaway house for couples/families or anyone looking for a serene weekend.

Guest favorite

Home in Lusby

4.96 out of 5 average rating, 134 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!

Guest favorite

Home in Montross

4.95 out of 5 average rating, 239 reviews

Stunning Lake House Retreat on the Potomac River

This beautiful lakeside home offers the perfect sanctuary for your next retreat, nestled along the Potomac River just two hours from the D.C. metro area. It is spacious enough for any large family gatherings or groups of friends. Lounge with a gorgeous view or start a ping pong/pool game. Whether embarking on your next fishing adventure, kayaking, biking, playing yard games or simply relaxing in our luxurious jacuzzi, your visit will surely be one to remember.

Guest favorite

Home in Lusby

5 out of 5 average rating, 168 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.

Guest favorite

Home in Lusby

5 out of 5 average rating, 133 reviews

Historic Rousby Hall, Waterfront, Patuxent River

*Heated pool open to 11/11/24* 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-November 11th) with amazing river views.

Guest favorite

Home in Reedville

4.95 out of 5 average rating, 229 reviews

Waterfront FamilyFriendly Home Improved for 2023

NEW IMPROVEMENTS for. 2023! Nautically furnished home on the water and a cul-de-sac which offers a relaxing and safe getaway space for guests. Large windows along the waterside provide for views from most rooms in the house. Watch the boats come and go from Smith Point Marina, or charter a boat for cruising or fishing.