Holiday houses in Dares Beach

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Top-rated holiday rentals in Dares Beach

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Guest favourite
A charming cottage exterior showcases a well-maintained garden with colorful flowers lining the pathway. The front porch features a welcoming entrance, while large windows provide ample natural light. A white picket fence frames the lush greenery that surrounds the home.
Cottage in North Beach
4.91 out of 5 average rating, 119 reviews

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

Top Guest favourite
A spacious living area is highlighted by a light blue wall and wooden accents. A brown leather sofa is accompanied by a round ottoman. Natural light fills the space from a nearby room, while a staircase with white railing leads to the upper level.
Home in Prince Frederick
4.96 out of 5 average rating, 81 reviews

Bay Getaway

Enjoy coastal living in your own house 2 blocks from the Chesapeake Bay with community beach and jet ski / kayak launch! Explore nearby trails for hiking and fossil hunting beaches! Take day trips to Washington DC, Annapolis, Solomons Island, North Beach, and Chesapeake Beach! Home features a fully stocked kitchen, an upper enclosed sunroom with winter bay views, and a fenced in yard with picnic table and space for kids to run around! Seasonal fishing, crabbing, hunting, duck hunting nearby!

Top Guest favourite
Apartment in Lexington Park
4.97 out of 5 average rating, 142 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.

Guest favourite
A serene coastal scene features a sandy beach lined with gentle waves. Overhanging branches with white flowers frame the view, while a distant pier is visible along the horizon. The sky is bright blue, accented with a few small clouds.
Cabin in Port Republic
4.8 out of 5 average rating, 20 reviews

Ocean Break

Your peaceful retreat by the beach. This cozy, private space offers the perfect setting to pause, breathe, and recharge away from the noise of everyday life. Surrounded by a quiet coastal atmosphere, it’s ideal for those seeking rest, reflection, or simply a relaxing getaway. While it feels like a hidden escape, you’re just 10 minutes from the shops and restaurants in Prince Frederick and only 20 minutes from the lively waterfront of Solomons Island, the iconic Tiki Bar.

Top Guest favourite
A wooden swinging bench is suspended under a wooden structure, surrounded by lush green grass and mature trees. Views of the bay can be seen in the background, providing a serene setting for relaxation.
Apartment in Port Republic
4.96 out of 5 average rating, 234 reviews

Serenity Suite on Chesapeake Bay

Come enjoy our waterfront home on the scenic Calvert Cliffs. Take in beautiful Bay views in Adirondack chairs with stunning vistas. Photograph wildlife. Comfortable ½ mile walk to private community bay shoreline. Have breakfast in the yard while enjoying the sunrise. Stroll the community shoreline and explore fossil hunting, hike at nearby trails. No pets are allowed because I have a severe allergic reaction to pet hair and dander. Thanks for your understanding.

Top Guest favourite
Apartment in Lexington Park
5 out of 5 average rating, 396 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Top Guest favourite
A bright sun porch features a round glass dining table surrounded by four light-colored chairs. Large windows provide views of the waterfront, allowing natural light to fill the space. A cozy seating area is visible in the background, offering a serene atmosphere.
Home in Leonardtown
5 out of 5 average rating, 146 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. Be sure to visit our sister property, Water's Edge Cottage.

Top Guest favourite
A peaceful sleeping area features a neatly made bed with floral-patterned bedding in blue tones. A wooden nightstand holds a book and a small plant, while a warm light illuminates the wall, creating a cozy ambiance.
Loft in Lusby
5 out of 5 average rating, 397 reviews

Chic Loft | Rest and Relax l Private Beach Access

Outage worker welcome: 1 guest. orefer night sleeper as we will come and go thru garage during the day and the dog will bark..We cant guarantee quiet daytime sleeping conditions Relax in a chic, private loft just 5 minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. Enjoy our private, above-garage hideaway with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home.

Top Guest favourite
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
4.97 out of 5 average rating, 262 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
A round wooden dining table is set with four matching chairs. On the table, placemats featuring a simple design are arranged. The kitchenette is visible in the background, equipped with white cabinetry and a small counter space. Light-colored flooring adds a warm touch to the space.
Guest suite in Lusby
4.84 out of 5 average rating, 166 reviews

New Light suite, appartment comfortable living

Guest Suite apartment , on the ground floor. located on the back side of the house. The apartment includes 2 queen beds, 50 inch TV, kitchenette, living room dining area, and full bath. This apartment is fully private with a private entrance on the backside of the house. (no shared spaces). Please include total number of guests.

Guest favourite
Apartment in Prince Frederick
4.78 out of 5 average rating, 32 reviews

Pop's Place

A cozy 600 square ft apartment located in the lower level of our home. It has a private entrance. The neighborhood is quiet. You can watch the birds and squirrels outside your door. The high ceilings make the area more spacious. It is an oasis for anyone who wants to just chill.

Guest favourite
Guest suite in Temple Hills
4.93 out of 5 average rating, 61 reviews

Newly remodeled efficiency apartment.

Close to 495 highway. Located mins. from National Harbor and Andrew's Airforce Base. Only 13 miles to the National mall and Smithsonian museums. 3.5 miles to cloestest metro station and a couple of blocks to a bus station. Separate entrance, own heating, and a/c, wifi, and tv included.

Popular amenities for Dares Beach holiday rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Calvert County
  5. Dares Beach