Apartment vacation rentals in Kent County

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Kent County

Guests agree: these apartments are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Rock Hall

5.0 out of 5 average rating, 78 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.

Jul 7 – 14

G$31,517 GYD per night

Guest favorite

Apartment in Chestertown

4.97 out of 5 average rating, 194 reviews

Centrally located, romantic escape in quiet area.

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), 2 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.

Sep 5 – 12

G$46,842 GYD per night

Guest favorite

Apartment in Worton

4.94 out of 5 average rating, 17 reviews

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.

Jul 4 – 11

G$36,500 GYD per night

Guest favorite

Apartment in Chestertown

4.92 out of 5 average rating, 63 reviews

1-br apt in downtown Chestertown

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.

Jun 28 – Jul 5

G$39,653 GYD per night

Apartment in Rock Hall

New place to stay

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 store, events, and more. A full kitchen, comfortable living room, private entrance and backyard access await you. Large grassy yard with firepit, BBQ grill, and picnic table. Great for playing or relaxing. This one bedroom apartment sleeps 4 comfortably.

Sep 5 – 12

G$28,048 GYD per night

Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 47 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.

Jan 20 – 27

G$45,975 GYD per night

Apartment in Rock Hall

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.

Dec 24 – 31

G$27,824 GYD per night

Guest favorite

Apartment in Chestertown

4.98 out of 5 average rating, 49 reviews

3 BR Patriot House- UNIT ONE /Mid-Century Modern

Mid-Century Modern decor thru-out this turn of the century home. Renovated in Fall of 2017 and decorated with attention to detail. For groups up to six. We have recently remodeled UNIT TWO which is the lower unit. These can be rented separately or together with locked door connecting both units. Located 1 1/2 blocks from Washington College and downtown. Early check-in and late check-out available. Front porch adds to cozy charm.

Jun 24 – Jul 1

G$62,971 GYD per night

Superhost

Apartment in Stevensville

5.0 out of 5 average rating, 3 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.

Oct 22 – 29

G$29,851 GYD per night

Apartment in Rock Hall

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.

Jul 11 – 18

G$68,540 GYD per night

Guest favorite

Apartment in Rock Hall

5.0 out of 5 average rating, 8 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.

Aug 30 – Sep 6

G$43,250 GYD per night