Apartment vacation rentals in Kent County

A cozy studio features a full-size bed with light bedding, complemented by a world map artwork on the wall. A seating area includes a chair and small table. Large windows allow natural light to fill the room, enhancing the welcoming atmosphere.

5 out of 5 average rating, 100 reviews

Inspiration Guest Suite - Cinnamon By The Bay

Inspiration is a cozy, bright studio with a full-size bed, seating area, kitchenette, and workspace. It is located upstairs in Cinnamon By The Bay's in-town suites. Main Street shopping, Java Rock coffee shop, and The Mainstay music venue are right outside the front entrance. Ferry Beach, Eastern Neck Wildlife Refuge, museums, charter fishing, kayaking, and marinas are a short walk or drive. Enjoy stunning sunsets and lively conversations on the community deck. Suite is limited to 2 guests.

The entrance features a bright blue door adorned with a seasonal wreath, flanked by two symmetrical windows. A paved walkway leads to the door, bordered by neatly arranged flower beds filled with pink roses. The overall setting presents a welcoming and well-maintained appearance.

4.96 out of 5 average rating, 24 reviews

Mermaid's Getaway

You will be close to everything in Rock Hall when you stay at this centrally-located ground-level apartment. Just 1 block from Main Street, park the car and walk to everything Rock Hall - shops, marinas, grocery store, ice cream shop, coffee, boat ramps, and more. A full kitchen, comfortable living room, private entrance and backyard access await you. Large grassy yard with firepit, BBQ grill, and picnic tables. Great for playing or relaxing. This one bedroom apartment sleeps 4 comfortably.

4.97 out of 5 average rating, 38 reviews

The queen-sized bed is dressed in soft bedding and accented by two pillows. A dark-wood nightstand and a small side table are positioned beside the bed, while an upholstered bench sits at its foot. Green accent walls and framed botanical prints enhance the serene atmosphere.

Apartment in Worton

Elliott House Historic Home Near Chesapeake Bay

The Elliott House is located outside of Still Pond, MD. Mere minutes to Betterton Beach (1.5 miles), Downtown Chestertown, etc A historic cottage built in 1854, this location was formerly an old time general store. In the early 1900's it was a stopping place for soldiers stationed at nearby training camps and the upstairs served as a makeshift dance hall. Current owner has kept the historic charm but added a number of modern conveniences. In the heart of Kent County with rural scenery.

A spacious studio interior features a king bed positioned near a sloped ceiling. A seating area includes a gray sofa and a recliner, complemented by a coffee table. A wooden dining table is set for two, and large windows provide ample natural light.

4.96 out of 5 average rating, 243 reviews

Private cozy cottage - center of Chestertown .

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.

The bedroom features a Queen-size bed with light bedding, complemented by a bedside table and lamp. A decorative chair and a small window allow natural light to fill the room, while a door provides access to the back porch.

4.9 out of 5 average rating, 81 reviews

1-br apt in downtown Chestertown (Unit 1)

Note: Beginning Oct. 4, 2023, we have eliminated all booking fees and cleaning fees. The price you see is the price you get. 1-bedroom newly-renovated apartment located in a 5-unit apartment building near downtown Chestertown, MD. Unit 1 is located two blocks from High Street (think Evergrain Bakery!) and about four blocks from the Chester River. Enjoy a shared front porch with the other long-term tenants, or use the private back porch to sit and read the newspaper or enjoy the outside.

A bright open living space features large windows allowing natural light to fill the room. Comfortable seating is arranged around a glass coffee table. The dining area is visible in the background, with a wooden table and chairs, connecting to a modern kitchen with stylish cabinetry.

4.98 out of 5 average rating, 103 reviews

Bright, new apartment in the heart of Chestertown

Flooded with light and in the center of all Chestertown has to offer. Have a front seat to Chestertown’s festivals. The apartment spans the entire front of the second floor of the recently restored building, built in 1877. Open living room/dining area/kitchen. Historic character with all modem conveniences, including dishwasher, washer/dryer, Smart TV and high speed wifi internet access. Off-street parking for one car on first come first served basis with ample street parking.

Apartment in Kennedyville

A comfortable living area features a neutral-colored sofa and armchair, accented with a patterned throw. A wooden coffee table is placed on a layered area rug. A TV is mounted on the wall, complemented by a bookshelf holding various books. The kitchen is visible in the background.

5 out of 5 average rating, 5 reviews

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...

A cozy living area features a light-colored sofas with decorative pillows, surrounded by two woven chairs. A round area rug adds warmth to the space. A small blue coffee table holds magazines, and natural light enters through a window, enhancing the room's inviting design.

5 out of 5 average rating, 18 reviews

DragonflyPeake Studio

Welcome to our cozy studio that we built for the comfort of our friends, family and Airbnbers. Our DragonflyPeake Studio is a centrally-located place. We are directly across from the Osprey and Haven Harbour Marinas and are in walking distance to the Ferry beach, Muskrat Alley for Breakfast and The Blue Heron for dinner and drinks. We are also a walk to town or bike ride. Enjoy a quiet cozy location with coffee or cocktails on the back deck.

Apartment in Stevensville

A serene sleeping area is highlighted by a large canvas artwork depicting a sunset over water. A stylish lamp with a unique design complements the soft white bedding. Decorative stars hang from the ceiling, enhancing the tranquil atmosphere.

4.98 out of 5 average rating, 49 reviews

Relax Inn

We welcome you to relax in this comfortable space for two with a plush king sized bed and a private bathroom. Enjoy the high speed internet and 50 inch smart TV. The kitchenette is equipped with a mini fridge, microwave, Keurig and a table for two. A coded entry will open into your private space that is attached to our home but separated by a locked door. We love to offer early check-in and late check-out as our calendar allows.

An open living area presents a blend of comfortable seating, featuring a bright red couch and neutral armchairs. A round glass dining table is set with an orange centerpiece. Large windows allow natural light to fill the space, enhancing the airy atmosphere.

4.83 out of 5 average rating, 23 reviews

Unique modern apartment with a view

Modern, stylish and airy 2 bedroom apartment overlooking Main St. in the quaint fishing village of Rock Hall on the Chesapeake Bay. 5 minute or less walk to the water, shops and really nice restaurant options. Fully outfitted w/full kitchen & overlook balcony, too! Please note that taxes, which are separate from Airbnb room charges and service fees, are due upon check-in. Those taxes are 11% lodging and state taxes.

The exterior of the two-story building is shown, featuring a yellow facade with a porch adorned by a sign reading 'Hickory Stick.' A seated area is visible on the porch, and a pathway leads to the separate entrance. Nearby, a utility pole and greenery can be seen.

4.93 out of 5 average rating, 15 reviews

Knot's Landing, spacious Apt. downtown Rock Hall

Welcome to Knot's landing - a spacious apartment located above one of Rock Hall's favorite shops in the quaint Main Street corridor. Steps outside of your front door you will find a coffee shop, sweets / bakery shop, farmers market, ice cream, and more! Use the provided bicycles for quick access to other restaurants and marinas. Perfect place to stay to enjoy Rock Hall, Chestertown, and surrounding Kent County.

A shared front porch features two wooden chairs with light-colored cushions. The porch is shaded by a wooden ceiling and complemented by white columns. The surroundings include greenery, creating a pleasant entrance to the home.