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Waterfront, Dog-friendly, Hot Tub, Peleton

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**

Bell Estates*Brand New*Bay View*Corner Cottage*

Bell Estates is a newly built corner lot across the street from the bay with peek-a-boo views of the water from Master bedroom & front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

Warm Home Overlooking the Chesapeake Bay

Sitting on the Chesapeake Bay, North Beach is a town where you are so close to things, yet can feel so far away. Only 45 minutes form Washington, DC, you can sit on one of three decks and gaze into the Chesapeake Bay, enjoying all that small town life has to offer. An open plan, with defined spaces, the house is at once cozy (with a fireplace) and spacious for a family. It is great for couples, adventurers, business travelers, and families. This is not a house for large groups or parties.

Club Carp North Beach - Steps to the Bay!

Calendar open for bookings in April 2025! Welcome to Club Carp North Beach. A charming and cozy cottage just 3 blocks to the Boardwalk/Beach. Renovated throughout with 3 bedrooms and 2 full baths. Perfect place for a relaxing, family vacation! This kid-friendly home has a large fenced side yard with swing set, play area for the kiddos, and lots of extra amenities with families in mind. Comfortable outdoor dining area with fire pit and gas grill. Just steps to restaurants, shopping, and bars.

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

Hannah’s Hideaway

Cottage style with water view of Rockhold Creek. Water taxi right out front of house to take you to local restaurants. Crabbing excursions or fishing charters available for extra cost. Dog friendly. Local restaurants all within 1 mile from location. Fenced in back yard. Picnic table and fire pit to have own personal crab feasts or cookout. Many local restaurants with outside musicians.Grocery store and gas/liquor stores within 5 minutes from house.

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Make wonderful memories. Great place for families and multi family groups.

Beach Home | King Bds | Firepit | Backyard Dining

Welcome to A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor.