Holiday rentals with outdoor seating in Chincoteague Bay

Salty Roots Retreat_Huge Yard_FirePit/Kids&Groups

Experience the perfect beach getaway in Rehoboth Beach.This stunning 5-bedroom, 2-bath home offers an open-concept kitchen and living area, ideal for family gatherings. Relax in the expansive private backyard featuring a deck and fire pit area—perfect for games and evenings under the stars. Just moments from beaches, restaurants, shopping, waterparks, and vibrant nightlife. Fully equipped kitchen, coffee bar, & all linens provided for your comfort and convenience. Book your dream vacation today!

hi-A-tus A-frame

Charming A-frame nestled in the heart of Ocean Pines. Open floor plan, softest sheets, flat screen TVs, high speed WiFi, in an amenity filled community surrounded by multiple beaches. 10 min from Ocean City and 15 min from Assateague! Sleeps 4 comfortably. Perfect for 4 adults or family. Must be 25 yrs old. Enjoy all that Ocean Pines has to offer including 5 pools, multiple playgrounds, yacht club and farmers market. Weekly rental during the high season. Please inquire about longer stays.

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Summer Oasis w Private Beach and River Views

Soak up the sun at our riverfront retreat with panoramic views! This modern, spacious home features 2 cozy firepits, a heated screened-in porch, game room stocked with board games, and full-speed WiFi and separate office perfect for remote work. Enjoy kayaking, paddle boarding, an open kitchen, gym, ping pong, with PacknPlay & high chair for the kids. Perfect for fun-filled family & friend getaways! No lifeguard on duty, swimming and use of all amenities/equipment on property are at own risk.

Cozy Camper, 2010 Brookstone RV - Waterfront

38 foot Fifth Wheel RV located at marina. Fully equipped kitchen, 1 bath and 1 bedroom with comfy King bed. Living space includes dinette with 4 chairs, sofa w/ full size air mattress and two recliners set up in front of a 42" flat screen TV. Heat and air provide the perfect accommodations no matter the weather. Enjoy sitting by the fire pit or explore the Bay on one of our two Kayaks. A stone's throw from Trade Point Atlantic, Key Bridge work site. Just 15-20 minutes to downtown Baltimore.

Large, Luxurious, Modern Home in central DC

Large, luxurious modern townhouse centrally located with a Walkscore of 93, featuring a large private roof deck fully equipped with a dining table, couch, grill, and great views. This recently remodeled 4 bedroom 3.5 bath luxury townhouse is located on a quiet street, yet close to many dining options on both 14th and 11th street. The house has 4 beds and a large convertible couch so can easily accommodate 10 guests, perfect for large groups and families. Additional bed available on request.

El Ancla

stunning bay sunsets and idyllic outdoor space at this peaceful waterfront home in prime 94th street location with amazing breeze. Recently rehabbed - new hardwood floors, bathroom, and brand new interior and exterior furniture. Bayfront deck with your own boat slip. Brand new casual comfort deck furniture. Remote work with a view! 10 min walk to beach, playground, community arts center, mini golf, bars. Beach chairs included. We can provide pack n play upon request

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Summer Camp Tiny Cottage Walk to the beach & shops

At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for a couples, friends, and small families! • King sized bed with smart tv on the first floor • Two twin beds in a cozy sleeping loft • Small kitchen with propane stove, Nespresso maker & living space with a smart tv • Patio w/ charcoal grill, solo stove, & dining table • Paddle board & floats Please read through our totally honest disclaimer below!