Vacation rentals in Kent County

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Top-rated vacation rentals in Kent County

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Guest favorite

The exterior of the cabin displays a rustic design with wooden accents and large windows that invite natural light. A spacious grassy area surrounds the structure, complemented by trees and landscaping. A small patio area is visible, offering a place to sit outdoors.

Farm stay in Chestertown

4.95 out of 5 average rating, 147 reviews

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.

Top guest favorite

A spacious lounge area features comfortable seating with a sectional sofa and two dark leather sofas. A modern coffee table sits atop an area rug, and a wall-mounted smart TV is visible. Natural light enters through several windows, contributing to the inviting atmosphere.

Guest suite in Joppatowne

4.99 out of 5 average rating, 163 reviews

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

Top guest favorite

A historic two-story house is nestled among lush greenery, featuring a muted grey exterior with bright red shutters. The inviting front porch is framed by trees, contributing to the home's serene and picturesque setting.

Guest suite in Chestertown

4.99 out of 5 average rating, 102 reviews

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.

Guest favorite

An updated kitchen features modern appliances, including a white refrigerator and a built-in stove. Light grey cabinetry is complemented by a spacious countertop with a subtle marble pattern. Shelves display decorative items, while a wall art piece adds a touch of color.

Home in Chestertown

4.97 out of 5 average rating, 34 reviews

Charming Haven on High

Featuring an open, updated kitchen, 2 bedrooms, 1.5 bathrooms for up to 4 guests. Explore historic downtown with unique shops, delightful dining options, & the Arts & Entertainment district that stretches to the Chester River, just a 5-min. walk. Numerous events, include the Tea Party Festival, Summer Concert Series, First Fridays, Downrigging Weekend, the Annual Dickens of a Christmas & Saturday morning Farmers Market. Steps from Washington College, it’s ideal for parents & alum visiting.

Top guest favorite

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.

Apartment in Rock Hall

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.

Top guest favorite

The exterior of a two-story house is shown, featuring a private patio with brick flooring. A wooden table with chairs is set under a large navy umbrella, providing shade. Lush greenery surrounds the yard, and clear blue skies are visible above.

Home in Chestertown

4.97 out of 5 average rating, 29 reviews

High Tide & Hound

Welcome to your perfect getaway in the heart of historic Chestertown! This charming home is just two minutes from the iconic High Street Wharf, where you can enjoy scenic views, fishing, and waterfront strolls. We’re proudly family friendly , pet friendly, so bring your furry friends along for the adventure. And yes, we also have a 420-friendly space. Whether you’re here for the festivals, the river, or just to relax this is your ideal place. Comfortable , private, and conveniently located.

Top guest favorite

A serene waterfront view reveals calm water framed by lush green trees. A small private dock is visible, featuring an orange kayak resting at the edge. The scene conveys tranquility, inviting relaxation amidst nature.

Guest suite in Chestertown

4.99 out of 5 average rating, 232 reviews

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.

Top guest favorite

A charming three-story house is nestled in a lush green landscape. The exterior features white siding, a front porch with a railing, and an American flag displayed on the left. Well-maintained lawns and shrubs surround the property, contributing to a welcoming atmosphere.

Guest suite in Chestertown

4.98 out of 5 average rating, 172 reviews

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)

Top guest favorite

A cozy living area features two brown leather sofas, a patterned rug, and a soft ottoman. A reading nook is created with a gray chair draped in a yellow blanket. Natural light streams in through a large window, with plants and bookshelves enhancing the space.

Home in Chestertown

4.97 out of 5 average rating, 137 reviews

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.

Top guest favorite

A spacious lawn is surrounded by tall trees, leading to a two-story house with a porch. Soft evening light casts a gentle glow, while a hammock can be seen suspended between two trees, inviting relaxation in the outdoor space.

Casa particular in Chestertown

4.92 out of 5 average rating, 157 reviews

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

Top guest favorite

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.

Apartment in Chestertown

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.

Top guest favorite

The exterior of a large, historic house is viewed from the river, surrounded by leafless trees and greenery. A deck is visible, along with a patio area featuring white chairs. The structure showcases multiple levels and a traditional architectural style.

Apartment in Chestertown

5 out of 5 average rating, 119 reviews

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!