Holiday rentals with beach access in Kent County

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

Ruby's Sea Glass Cottage near Betterton Beach

This cute 1900 cottage in the center of Betterton has a full kitchen & three beautiful outdoor porches to unwind. There's one bathroom ON THE FIRST FLOOR (shower only). An outdoor shower is available seasonally! There are three bedrooms-ALL ON THE SECOND FLOOR. Enjoy the beach down the street to find sea glass or watch the sunset! SEE LISTING PHOTOS FOR INFO ABOUT THE AREA. BETTERTON DOES NOT HAVE A GROCERY STORE. Kids items upon request. Furniture/decor may be change from listing pictures.

Eastern Neck Water Paradise w/Brick oven & Beach

This beautiful breathtaking waterfront home is the perfect place for your vacation. This spacious 3 story house sits along the back waters of the Chesapeake Bay, along Grey’s Inn Creek with it’s own private pier and beach area!! Kayaks and paddle boards available for guests to use! The water is 6’-9’ deep depending on the tide. You can bring your own boat or if you’re interested in renting one, Lankford Bay Marina is only 15 minutes by car or boat, must have a MD boaters safety card to rent

Traveler Guest Suite @ Cinnamon By The Bay

The Traveler offers a private bedroom and fully equipped eat-in kitchen. For those guests who prefer separation from their dining area, but don’t need a separate living space, Traveler is a perfect match. Enjoy the comfort of not being awaken when someone sneaks a midnight snack, all while being easy walking distance to Rock Hall's shopping, coffee shop, restaurants, music venue, and festivities. It is one of our pet-friendly suites with easy access to the community back deck and rear yard.

Holiday Escape to the Riverside

Relax with the whole family or big group at our peaceful river home. Huge waterfront property. Bedroom, dining and living room river views. River and tidal beach access. Kayak, SUP or canoe. Enjoy backyard games, outdoor dining, hammock or fire pit. Massive waterfront screened-in porch with 2 dining and 2 seating areas. 10 min walk to adorable historic downtown. Festivals, art galleries, bakeries, ice cream, shops, spa & playground. This is our happy place - we hope it becomes yours!

Walking Distance to Marinas & Main St!

Ahoy! Embark on a wonderful vacation at “Welcome Aboard!" Our adorable home is within walking distance of waterfront marinas, restaurants, and the downtown strip, with coffee shops, stores, and more! Enjoy your morning coffee while sitting on the porch in locally purchased Adirondack chairs, then head into town to enjoy everything Rock Hall has to offer! Many of the pieces of artwork you see in our home were purchased from a photographer in town and custom framed by a nearby craftsman.

Bamboo Sands Villa & Captains Lookout

Where luxury meets coastal by the bay. A perfect spot to make memories, enjoy the views from the house or the hot tub, and we offer a WOOD BURNING FIREPLACE! Welcome to Bamboo Sands Villa & Captain’s Quarters, A peaceful retreat on the Chesapeake Bay where families can RELAX & reconnect. Here, serenity and fun flow as easily as the coastal breeze. Enjoy sandy beaches without the crowds, the sounds of waves on the bay without the oceanfront price tag, a coastal luxury getaway...

Cozy 1920's Bungalow Near Water/Local Attractions

Updated 1920's bungalow near all Rock Hall has to offer. Blocks away from the Bay, marinas and center of town. Coffee shop, grocery and other shops 2 blocks away. Walk to several restaurants. Cozy and very comfortable. Quiet street, and peaceful at night. This house is an ideal Rock Hall location. This home is well stocked, so most condiments, coffee, tea, sodas and water are included. There are also many toiletry and first aid products. No need to bring soap or shampoo.

Goose Haven, new waterfront house on Fairlee Creek

Goose Haven is nestled on 2 wooded acres on freshwater, Fairlee Creek - about 1.5 hours from Baltimore, Philadelphia, and Washington D.C. It is a very secluded, brand new, 4 BR, 3 BA, waterfront house with direct water access, a dock, and plenty of room to enjoy the outdoors. There is also a public boat ramp/launch right down the road. If you don’t have a boat, don’t worry, we have a kayak & canoe for you to use. Chestertown and Rock Hall are only 20 minutes away.

Mac's Waterfront Wonder

Your family will be wowed by this NEW waterfront 5 bedroom home with a home office, TWO balconies. Indulge in birdwatching (spot a bald eagle? ), boating and jet skiing! Visit Baltimore, DC, Philly, Golf and more! This new home is ideal for large families, long-term stays, or remote work. Three Queen beds; two twins and a bunk bed (full + twin). Sofa bed/queen and air mattresses for five more guests at an additional cost.

Bayside bungalow cottage by the sea

This quaint Cottage is located on a quiet residential road with quick access to the water. Located in Rock Hall, Maryland, guests will enjoy a getaway from the hustle and bustle of major cities. The Cottage boasts 1 bedroom and 1 bathroom, equipped with a private sauna. Guests are guaranteed to have a relaxing stay here at the Cottage House! Great views of Swan Creek and the Cheseapeake Bay.

River Cottage, Chestertown

Relax on the scenic Eastern Shore. We are located just off the Chester River. Step away from the hustle and bustle to our cozy cottage appointed with modern amenities. Our property is enjoyed my families and friends. Our tranquil backyard offers a fire pit and picnic table for entertaining We have bikes and kayaks for guests to enjoy while they unwind 15 mins from Washington College