Holiday houses in Dares Beach

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 --

Family · Value · River

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Custom waterfront home with everything you need to relax and recharge. Two levels of decks offer amazing views of the changing tides on Cat Creek. Soak in the hot tub and watch the eagles soar by, or head down to the dock for crabbing, fishing, and kayaking during high tide. Located in historic Southern Maryland, this quiet, hidden estuary makes for a unique getaway with great amenities. Fast WiFi for work, game room for fun, and a fenced-in yard for dogs. 1 hour from DC but feels worlds away.

Family · Value · Sleep quality

Chesapeake Escape Southern Md, Bay Adventures!

Come stay with us at Chesapeake Escape in Prince Frederick, MD. Stylish Chesapeake retreat just one block from the Bay! Enjoy fossil hunting, hiking, sunrise views, and take day trips to DC or Annapolis. Launch jet skis or kayaks from the nearby community ramp, and enjoy seasonal crabbing, fishing, and hunting. Newly renovated with a peaceful, modern design, it’s ideal for couples, small or large groups, families, or solo travelers. Settle in with fast Wi-Fi, smart TV—your coastal escape awaits!

Family · Location · Condition

Cozy Cottage by the Bay

The cozy, quaint cottage is nestled in a private bayfront community. Located two blocks from the water, you have access to both a boat ramp and private beach. Calvert county has so much to offer: fossil hunting, museums, hiking and beaches. Located near Calvert Cliffs, Chesapeake beach, and Solomon's Island. It is also an easy day trip to Washington DC. Enjoy the bay scenery and coastal birds from our brand new large deck. Conveniently located three miles from restaurants and shopping.

Family · Nearby · Condition

Blue Pearl-Luxury estate with private dock/jacuzzi

The Blue Pearl is a luxurious river front estate with a private pier to catch crabs, fish and kayak. Soak in the outdoor jacuzzi and enjoy the river life. Three bedrooms with three full bath en-suites and over 2800 square feet of luxury accommodations await you. Office has Queen sleeper sofa. Pull up to your private boat dock, catch blue crabs with the provided traps, toast s’mores in the firepit while sitting in your Adirondack chairs. Enjoy two decks to view the sunrises and sunsets.

Family · Value · Sleep quality

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

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 dates**

Value · Location · Indoor spaces

Luxury Farmette -Private & Secluded-1hr to DC

Plan your tranquil getaway to the countryside and escape to a luxury dream farmhouse. Located on 5 acres, the renovated home offers peace in a quiet, private location. Guests have access to a pool and outdoor shower, fire pit, a covered grilling area and a playground for children. The home is located approximately 1hr from Washington DC and is the perfect place for a retreat, family vacation and everything in between! Plenty of parking available for those traveling with boat/camper/RV.

Location · Family · Heating

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

Family · Location · Breakfast

Waterfront Home: Osprey Getaway

Welcome to The Osprey Getaway! This spacious home is the perfect destination for families seeking a relaxing retreat. Our home is not far from Solomon’s Island, Patuxent River Naval Air Station, St. Mary’s College of Maryland, and historic Leonardtown. Here you'll find an open floor plan and plenty of space to unwind and take in your surroundings. Enjoy the peace and quiet of Cuckold Creek and the beauty of our newly renovated home. We can't wait to share our home with you!

Family · Value · Outdoor spaces

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.

Value · Family · Air conditioning

Waterfront on St. Leonard Creek at Fort Hill

Waterfront home on St. Leonard Creek w/ private pier for fishing and relaxing, PLUS a small beach area. Close to Solomons, fossil hunting at Calvert Cliffs, the Calvert Marine Museum (and their concerts), and other area attractions. Forget stairs! Our elevator directly connects the parking area to your private floor! Fort Hill is a uniquely quiet and private space with wide-open views of the outdoors. 4 kayaks are included FREE for you to enjoy!

Location · Family · Hiking

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).

Location · Family · Decor