Apartment holiday rentals in Kent County

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.

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.

Relax Inn

We welcome you to relax in this comfortable space for two with a plush king sized bed and a private bathroom. We love little people and have a pack and play. ☺️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.

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.

Turtle Cove Room at Still Pond Inn

Welcome to the Turtle Cove Room at Still Pond Inn, a bright coastal guest room featuring a queen bed with a pillow-top mattress, layered textures, and coastal accents that make the space feel fresh and inviting. Guests can enjoy a private en suite bathroom with a tiled walk-in shower, glass doors, built-in shelves, soft towels, and fresh bath essentials. The room also includes cozy lighting, and a quiet sitting area for morning coffee, reading, or unwinding after a day out.

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...

Last-Minute Retreat Center of C’town -1 night stay

Escape to a secluded studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of private gardens. Relax in front of the fire with views of gardens in the windows. Kitchenette has large toaster oven, hot plate, microwave, fridge, and Keurig/drip coffee makers. We have an under counter filtration system for pure delicious drinking water. King bed with deluxe linens and mattress, washer dryer Same property listed on Airbnb for less with 2

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, 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. Pet-friendly for an additional fee.

Beachcomber Suite at Still Pond Inn

Step into serenity at The Still Pond Inn’s Beachcomber Suite, a 456 sq ft ground-floor retreat blending historic farmhouse charm with modern comfort. Enjoy a private entry, bright living area with queen pullout sofa, a queen bedroom with fireplace, kitchenette, and spa-like bath. Shared perks include a screened porch, lawn, grill, and endless coffee. Close to Chestertown, Rock Hall, beaches, and marinas—ideal for couples, solo travelers, or small families.

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.

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.

114 High Chestertown Lux 1st Floor Apt w/ Patio!

Experience the charm of Chestertown, Maryland by indulging in a stay at our upscale vacation residence. Located just a stone's throw away from the vibrant town center, you'll find a plethora of shops, cafes, and restaurants waiting to be explored. Close to the Chester River landing for Tea Party, Downrigging and more! Perfect for a romantic weekend getaway!