Holiday houses in Cobb Island

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Top-rated holiday rentals in Cobb Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

An aerial view captures the waterfront home surrounded by lush greenery with a private dock visible by the water. The neatly maintained property features landscaped lawns and nearby homes, illustrating a serene setting alongside Neale Sound.

Home in Cobb Island

4.99 out of 5 average rating, 139 reviews

Waterfront 4-BR home w/ hot tub & charging station

Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

LocationFamilyOutdoor spaces

Top Guest favourite

A wooden dock extends into calm waters, showcasing a boat moored at the end. The serene surface reflects the pastel colors of the sky during dusk. Wooden posts line the edges of the dock, enhancing the tranquil setting.

Home in Newburg

4.91 out of 5 average rating, 128 reviews

The River House, a Wicomico Beach Retreat

Located right on the water of the Wicomico River with a private sandy beach, The River House will become your favorite retreat! This 5 bdrm, 3 bath fully stocked home has all the convenience of modern construction (including wifi) but maintains the vintage charm of the original property. The acre+ plot is very private with spectacular forest & water views. Fun can be found in every direction and for all ages! It has two bottom floor bed/bath combos, plus a fabulous sleeping loft for the kids!

LocationFamilyPets

Top Guest favourite

A circular stone fire pit is surrounded by six blue Adirondack chairs, set on a brick patio. The spacious yard features grass and trees, with a glimpse of the house in the background and colorful clouds in the evening sky.

Home in Colonial Beach

5.0 out of 5 average rating, 101 reviews

Lovely 5 bedroom home, TVs in all bedrooms.

Escape to this spacious and inviting 5 bedroom home, perfectly situated in a quiet neighborhood just a short walk from the beach. Designed for comfort and convenience, the well appointed kitchen is ready for home-cooked meals. A premium propane grill is also provided for our guests. Each bedroom is equipped with its own TV ensuring relaxation for all. There is a large fenced backyard with a fire pit perfect for relaxing under the stars. Pets are welcome. The home is also handicapped accessible.

FamilyLocationCleanliness

Guest favourite

A wooden pier extends toward a grassy area lined with two charming cottages. The structure features sturdy wooden posts on either side, inviting guests to enjoy the tranquil view of the river and the surrounding greenery.

Cottage in Cobb Island

4.93 out of 5 average rating, 103 reviews

Happy Hour~Private dock, amazing sunsets, peaceful

Perfect for a private, scenic romantic get away or for a group of 4. Open for short- and long-stays. ‘Happy Hour’ is a uniquely furnished 2 bd/2 ba riverfront cottage at Cobb Island, Md, where you can chill to your heart’s content with panoramic views & sunsets on the Potomac River. Drop anchor! 2 bikes. Great fishing. 2 TVs, Wi-Fi, fully-equipped kitchen, W/D, deck, charming 1,100 sq.ft., 40s home. Enjoy the serenity. 3-ni. minimum reservation. Sleeps 4 max. No partiers. Unforgettable home!

FamilyLocationHospitality

Top Guest favourite

A private entrance is visible on the exterior of a modern home, featuring a vibrant blue door framed by a welcoming porch. An outdoor seating area includes a round table with four dark chairs, complemented by blue cushions. A decorative sign adds charm to the space.

Holiday home in Colonial Beach

4.95 out of 5 average rating, 175 reviews

The Observatory on Rose Manor

The Observatory on Rose Manor is a private home. It’s 2 blocks from the heart of downtown & beach. Colonial Beach is the golf cart capital of Virginia, we all drive them here. Rent one when your in town. Just over an hour south of DC. This small town takes you back in time with events & local charm. This brand new rental is on the grounds of Rose Manor. Rose Manor was built 1896 it operated as the New Willard hotel for over 50 years. Come relax on its huge porches & enjoy the water view.

LocationValueRiver

Top Guest favourite

Home in Cobb Island

4.97 out of 5 average rating, 101 reviews

*Solitude At Sunset*

YOUR WATERFRONT OASIS AWAITS! If you are looking for a true getaway, look no further. Tucked away on a small, peaceful island, this hidden gem is uniquely surrounded by 3 bodies of water: The Potomac River, the Wicomico River, and Neale Sound. This quiet island oasis offers the perfect place to step away from the busy world! This cottage is incredibly special to us. For four generations, it has been a sanctuary for our family-filled with love, laughter, and countless memories.

LocationFamilyDecor

Top Guest favourite

A private dock extends into the calm water, featuring a wooden platform and seating areas. A vibrant blue paddleboard rests on the grassy shoreline, while an in-ground trampoline is seen nearby. The scene is framed by trees under a clear blue sky.

Home in Montross

4.97 out of 5 average rating, 108 reviews

Waterfront home, private dock

Relax right next to the water in this tranquil Montross getaway. Fish, crab, kayak, paddleboard, or just sit on the swing and watch dolphins, eagles, herons, and stingrays from your private dock. Dine outdoors on the spacious deck, spend some some quality family time with an in-ground trampoline, tree swing, cornhole, bocce ball, spikeball, and a unique custom-built treehouse. Or just stay inside, relax, and enjoy the views, with an indoor electric fireplace and jacuzzi bathtub.

LocationValueTV

Top Guest favourite

A view from the property shows a grassy area leading to the water. A screened porch is visible, providing a tranquil space. The river reflects the blue sky and fluffy clouds, with trees lining the opposite bank. A wooden dock extends into the water.

Guesthouse in Bushwood

4.94 out of 5 average rating, 186 reviews

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

FamilyLocationQuiet

Superhost

A spacious outdoor area is equipped with shaded seating, including a sofa set and a coffee table, arranged on a patterned rug. A hammock hangs in the background, and a fenced yard provides a private setting, surrounded by trees for a tranquil atmosphere.

Home in Colonial Beach

4.98 out of 5 average rating, 138 reviews

Riverview on the Potomac

Relax and unwind at 'Riverview on the Potomac'. • 5 mins drive to pier and beach access • 15 min to Ingleside Vineyards • Fully equipped backyard with outdoor kitchen, bar, hammock swings, fire pits, and plenty of seating to enjoy with your family and friends • Large jet tub in the master bathroom • Beach necessities (toys, wagon, chairs, umbrella) • Family Friendly: high chair, pack-n-play, baby gate, and board games • Two dedicated workspaces for days you need to work

ValueFamilyView

Guest favourite

A window frame is visible, showcasing a scenic view of the Potomac River. A telescope is positioned within the frame, aimed towards the tranquil waters. The horizon features trees and a distant shoreline, while a wooden fence adds a touch of structure to the foreground.

Home in Montross

4.86 out of 5 average rating, 103 reviews

Potomac River Getaway

Discover an incredible escape at our cliffside gem on the Potomac! This 3BR, 2.5BA retreat has airy living spaces and panoramic river vistas from the wraparound deck. Enjoy your coffee as eagles soar above, and unwind in a private hot tub beneath star-filled skies, all while soaking in breathtaking riverside sunsets. Perfect for family and friend getaways, with historical sites close by. Montross’s small-town charm awaits your exploration—enjoy!

LocationValueBathroom

Top Guest favourite

A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.

Home in Leonardtown

4.99 out of 5 average rating, 139 reviews

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”).

FamilyValueAmenities

Superhost

An aerial view of a waterfront property showcases a red-roofed home bordered by lush green grass. A private pier extends into the calm water, while a play area with a playset sits adjacent to the house, emphasizing the outdoor living space along the Potomac River.

Home in Newburg

4.91 out of 5 average rating, 101 reviews

Peaceful waterfront home, 1-hour from DC

Beautiful home with stunning sunset views on the lower Potomac River. Home features a private pier, fire pit, theater room, and play area for kids! Only 1 hour from DC, 90 mins from Richmond. Easily accessible from anywhere in the DMV area. Full kitchen, and large screened in back porch. This is a vacation home-come true.

LocationValueGetting around