Ferienunterkünfte in Kennedyville

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.

Cozy, clean & spacious lower level of a new home

This is a spacious lower level of a newly built home. This private guest area has a lounge, dinning, and kitchenette in addition to a bedroom and a bathroom. Guests share only the main entrance of the townhouse with owners who live upstairs. This private decorated space includes a smart TV, comfortable seating, dining for 4, microwave, coffee maker, full refrigerator, toaster/air fryer, queen bed, wardrobe & dresser. Washer/dryer available upon request. Please review house rules before booking

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.

House On The Hill - Historic Private Second Floor

This Guest Space is the full second floor. Have the second floor to yourself, w/private bathroom, sitting area, and two bedrooms. NOTE: host live on the first floor. The family cat Andy might pay a visit (friendly). You use the front door and go right up the steps to your space. The shared part is you can see our space on the stairs and thus may here us but we are quiet. Walking distance to town! Hang out outside & enjoy chairs and a fire-pit if you wish, or take the 5 min walk downtown.

Chestertown - Eastern Shore Getaway

This century-old three-story home is in the beautiful historic district of Chestertown on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue. (NOTE - Airbnb adjusts our rate according to the current demand for rooms)

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Private 1BR/1BA | Home Comfort & Hotel Perks

Prime Location | Hotel Amenities w+ Home Comfort Less than 5-30 min to shopping, hospitals, BWI, & attractions! This suite blends hotel ease w/ home comfort—perfect for professionals & remote workers. ✔ Work & unwind – Sit-stand desk + Smart TV ✔ Stocked & ready – Coffee, snacks, mini fridge & microwave ✔ Rest well – Queen bed, satin pillows & blackout curtains ✔ Spacious storage – Walk-in closet, drawers, iron & mirror ✔ Self-care & fitness – fitness gear, beauty products & yard accessory

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

Chestertown Private cottage with NFL Sun Ticket

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

Sweet Bay Overlook

Take it easy at this unique home overlooking the Chesapeake Bay. You will enjoy watching the amazing sunsets on the bluff as the eagles, ospreys and boats drift by. Our little house was built in the 1960’s by a brick mason who was very good at his trade. In recent years, the home had fallen into disrepair, but a talented Amish craftsman purchased the house and renovated it from top to bottom. The Sweet Bay that you see today reflects his incredible attention to detail and quality.

Grandma’s Cottage

If you like antiques and old time charming cottages…this is the place to stay. The cottage was built in 1950 and has 2 bedrooms with 2 twin beds in each room. A living room, kitchen and screened front porch. It is a 8 minute walk to the beach from the cottage. It is quiet and cozy and a good size cottage for 4 people.Sheets and towels are all provided.Along with beach chairs, towels and an umbrella and inflatable floating river tube. Parking by the cottage for 2 cars.

UpStairs at KBM

Centrally located in the middle of nowhere says it all. Kennedyville is found in the Heart of Kent County, in the Heart of the Eastern Shore of Maryland, the Land of Pleasant Living. Kennedyville is an unincorporated town situated on State Road 213: 10 minutes south of Galena, with its Antique stores and Twinney's, 10 minutes north of Chestertown with everything else. Cozy, well appointed and with the possibility of a Chef's Breakfast in the morning? Hmmmmm...