Vacation rentals in Romancoke

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

The Pool House in Romancoke on the Bay

Spacious 4 bedroom home on Kent Island minutes from multiple wedding venues. Inground pool with sunny & shaded sitting areas for everyone to enjoy. Pergola brick patio w/table & a deck with a bar for outdoor meals and a fully fenced back yard for your dog. Additional fee per dog. Living room with Fireplace, Sunny family room, nicely equipped Kitchen, all just a block from the Eastern Bay if you have beach strolling, kayaking or paddle boarding in mind. South Island Bike Trail just a block away.

Cheerful & Spacious Shore Life Beauty!

Welcome to our charming yet peaceful abode & island oasis where sailing, marine life, & bay exploration exceed the standard! This exceptional home is conveniently located to a variety of high quality restaurants, parks, outdoor activities, spas, beaches, wedding venues, & other entertainment including live music, hunting, & antiquing while also being 20-minutes from Annapolis & 1-hour from Baltimore City & DC. Let this be your definitive choice for a magical destination you'll forever remember.

Bayview Bungalow - Water view, EV charging station

One level living with a view across the Chesapeake Bay of the most amazing sunsets over the Annapolis skyline. Enjoy the large fully stocked kitchen, spacious bedrooms, claw foot tub & separate shower, deck, bbq grill, fire pit, & yard. Take the bikes on the local trails, nap on the hammock, play corn hole, take the beach chairs/toys to the private neighborhood beach, go to one of the many excellent restaurants, visit historic Stevensville, take a trip to Annapolis or DC, & so much more!

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay

Plan your getaway on the Chesapeake Bay! Blue Heron’s Landing is on beautiful Kent Island, MD. The home is a short walk from scenic waterways and beautiful biking and walking trails, and a quick drive to fantastic dining options and several Maryland’s best wedding venues. This hidden gem is just across the Bay Bridge from Annapolis and 1 hour from DC and Baltimore. It’s the perfect place to disconnect and recharge, or use as a launching point to explore more of Maryland’s Eastern Shore.

Waterfront | Swim Spa + Sauna + Beach + Game Room

Escape to Oyster Bay Getaway, a stunning 4-bedroom waterfront retreat designed for relaxation and fun. Enjoy serene water views throughout the home, unwind in the swim spa or sauna, and cozy up by the indoor fireplace. Step outside to a private dock and fire pit perfect for evenings under the stars. The garage game room (unconditioned) and indoor lounge with poker table make this the ideal getaway for families and groups seeking comfort, entertainment, and a true waterfront experience.

Relax on Kent Island in 4 Bedroom Home w/Waterview

Enjoy your vacation in this Beautiful & Stylish 4 Bedroom Home with a view of the Chesapeake Bay! Perfect for Families & Wedding Groups. We are conveniently located to many areas/cities: Annapolis- 20 miles Baltimore- 45 Wash. DC- 50 Easton- 35 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions. This is a Non-Smoking House. Also No Pets or Parties & 11 max guests (8 max adults). Book Today!

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

Bayside Escape

Enjoy a relaxing stay at a family friendly home on the Eastern Bay. Bask in rosy hues as the sun sets over the Eastern Bay from the covered deck or the living room couch. Observe marine life in its natural habitat off of the dock. At our Bayside Escape you get two choices for how to cool off- float in the swimming pool or take a refreshing dip in the bay itself! This charming home has it all- space to work, play, and relax.

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.