Apartment vacation rentals in Kent County

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.

4.97 out of 5 average rating, 230 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 every window. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), two burner hot plate, microwave, refrigerator, and Keurig/coffee makers. Comfortable king bed with luxury linens, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

A private bedroom features a spacious bed adorned with a patterned bedspread. Two bedside lamps provide soft lighting on either side. Light filters through a window with blinds, highlighting the wall's calming shade and the neutral-toned carpet underneath.

4.97 out of 5 average rating, 30 reviews

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.

Guest favorite

The living room features a soft blue couch alongside a comfortable armchair. A small dining table with white chairs is positioned near a window, providing natural light. A wall-mounted television is visible, and a door leads outside.

4.9 out of 5 average rating, 78 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.

Guest favorite

A spacious living area is furnished with a light-colored sectional sofa, arranged with a coffee table and an accent table. A stone fireplace serves as a focal point, complemented by a ceiling fan above. Natural light enters through the nearby door.

Apartment in Worton

5 out of 5 average rating, 7 reviews

Country Living 3 Bed Historic Cottage Apartment

The Elliott House was built in 1854 and served as a general store and in later years a sporting goods & hardware shop. The owners have restored the residence, keeping many original characteristics but making comfortable for 21st century guests with wi-fi, central heat/AC, smart TV’s, & more! Spacious private backyard enclosed by bamboo and foliage. Tastefully appointed with outdoor Amish crafted furnishings. Only 1.5 miles to Betterton Beach and 10 minute drive to historic Chestertown.

A well-appointed sleeping area features a queen-size bed with a light blue coverlet and decorative pillows. Two nightstands with lamps flank the bed, and a window allows natural light to fill the room. A chair and small desk are visible in the corner.

5 out of 5 average rating, 15 reviews

Still Waters Suite - Cinnamon By The Bay

Still Waters is a studio suite with a corner view of downtown Rock Hall. It hosts a queen-size bed, fully-equipped kitchen, dining/work table, and private bathroom with bathtub/shower combo. Located upstairs, it hosts a wonderful vantage point of Rock Hall’s festivals. Leisurely walk to boating/fishing charter excursions, restaurants, Ferry Beach, and shopping opportunities. Enjoy stunning sunsets and lively conversation on the community deck located at the rear of the building.

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, 88 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.

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, 11 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.

4.97 out of 5 average rating, 37 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.

Guest favorite

A cozy living room features a light-colored sofa paired with a wooden coffee table. A television is positioned on a console table, and natural light filters in through a nearby door leading to a small patio area. The floor is adorned with a textured area rug.

5 out of 5 average rating, 12 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 modern living area features a comfortable gray sofa adorned with decorative pillows. A sleek, linear fireplace is built into a stone wall, while overhead beams add architectural interest. The space is complemented by a kitchen island in the background, with pendant lighting and bar stools.