Holiday houses in Rose Haven

Getaway by the Bay

Forget your worries in this spacious and serene getaway. Located less than an hour from DC/Baltimore, you’ll find this comfy getaway tucked across from the Chesapeake Bay and right around the corner from restaurants & bars, shops, boardwalk, and marinas. This private home boasts cozy furnishings, indoors and out, with plenty of space to relax with family and friends. With 4 bedrooms, 2.5 bathrooms, large open kitchen and living room, front and back outdoor lounge with fenced in yard and firepit.

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!

Charming 1BR Bungalow Guest Suite | Close To Water

Fairly new construction with separate entrance; 1BR guest suite with a mini bar, a full bathroom with a gorgeous stand up shower & bench. You can see the water from the driveway. Your guest suite was built as a new addition to the classic 1940's bungalows that define North Beach. Tastefully furnished with various artwork displayed throughout the unit. The guest suite is located in North Beach, MD, only several mins walking distance to restaurants, shops, boardwalk pier, beach & Chesapeake Bay.

Beachside Oasis | King Suite + Beach Passes

Welcome to Bay Haven at A Haven Away! Relax in a fully-equipped, plant-filled oasis with a king bed primary suite that our guests love. Its prime location is in walking distance to the beach, restaurants, fresh seafood, and wetlands. We’ll share our beach passes and lots of local recommendations so you can enjoy our little slice of heaven. 12 min walk to the beach, boardwalk, restaurants, and kids play areas in cute North Beach, MD 7 min drive to Herrington Harbor 14 min drive to Tacaro Estate

Above the Bay - Walk to the Beach

Wake up above the Chesapeake Bay at this cozy North Beach retreat with sweeping wetland and water views from the private third-story deck. “Above the Bay” is the perfect spot to relax, sip morning coffee at sunrise, and enjoy the peaceful coastal vibe. Located just steps from North Beach Boardwalk, restaurants, shops, and the beach, this charming getaway offers the best of small-town waterfront living with all the comforts of home. Perfect for couples, solo travelers, or a quiet weekend escape.

Chesapeake Escape

Chesapeake Escape is a completely rehabbed home within walking distance of Herrington Harbor, Ketch 22, and the Chesapeake Grill/Deli. Not far to Annapolis,DC,&Calvert County; which has a boardwalk,public beaches,water park,boat rentals(crab/fish) & casino! Our 4 bedroom, 2 bath home accommodates up to 14 people with a completely stocked kitchen. There are 4 tv's inside the home plus games for children, as well as adults. Nice size back yard has a tiki bar with a tv and dining area. STR00986

Charming Historic 2 Bedrooms on the Chesapeake Bay

Come visit North Beach, Maryland! Enjoy year-round activities, crab houses, and great restaurants. Our quaint 100-year-old cottage sits directly on the Chesapeake Bay. Relax on the front porch and watch the sunrise. Take a short walk to the charming shops and eateries. The comfortable cottage has everything you need for a getaway. Just a stone’s throw away from the half-mile-long boardwalk and bike trails. Stroll to the Saturday morning Farmer’s Market, First Fridays, and movies on the beach!

Waterfront Lux Cottage With Amazing Views Near DC

Welcome to Rowan's Rendezvous! Relax with the whole family at this renovated 1930's bungalow. This waterfront front home offers a unique, peaceful vacation experience for up to 6 guests (2 bedrooms, 1 sofa-queen bed). As a waterfront property, it provides breathtaking views of the Chesapeake Bay with family-friendly amenities (e.g., child roller coaster, sandbox, children toys / books, pack-n-play, etc.). The property features a private parking lot for up to 4 cars and a full kitchen.

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**

The Cottage at Broad Creek

Your Private Waterfront Escape on Maryland's Eastern Shore Wake up to panoramic water views from your soaking tub. Kayak from the private dock, cook your catch in the chef's kitchen, then gather at your waterside fire pit and grill as the sun sets over the bay. Minutes from historic St. Michaels yet secluded enough to feel like your own sanctuary. Perfect for couples seeking both adventure and relaxation, whether celebrating a milestone or simply unplugging together.

The Licorne Beach Cottage

Welcome to "La Licorne" Waterfront Cottage! Escape to our cozy waterfront cottage, a perfect getaway for families and friends looking to unwind by the water. It is a quick getaway from the hustle and bustle of Washington, D.C, and it is nestled just steps away from the Chesapeake Bay. This newly renovated beach cottage blends the vintage character with modern comforts, creating an inviting and relaxing atmosphere. No pets allowed.

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.