Vacation rentals in Kent County

4.95 out of 5 average rating, 39 reviews

An outdoor seating area is set on a wooden deck, featuring a large table surrounded by light blue chairs. A fire pit is visible in the foreground, with lush greenery and a sandy beach in the background, along with the home and upper deck partially shown.

Home in Middle River

Waterfront Home with Private Beach, Stunning Views

Escape to paradise at our Chesapeake Bay waterfront vacation home in Oliver Beach! Our home is the ideal place to unwind and appreciate the beauty of Chesapeake Bay. You'll love the stunning views, the private beach, the spacious upper deck and the beachside deck surrounded by trees. You'll have so much fun fishing, swimming, kayaking, paddle boarding, or just relaxing by the water! It's the perfect spot for a dreamy retreat, a romantic sojourn, or for shared fun with group of friends or family.

4.96 out of 5 average rating, 51 reviews

Eastern Neck Water Paradise w/Brick oven & Beach

This beautiful breathtaking waterfront home is the perfect place for your vacation. This spacious 3 story house sits along the back waters of the Chesapeake Bay, along Grey’s Inn Creek with it’s own private pier and beach area!! Kayaks and paddle boards available for guests to use! The water is 6’-9’ deep depending on the tide. You can bring your own boat or if you’re interested in renting one, Lankford Bay Marina is only 15 minutes by car or boat, must have a MD boaters safety card to rent

4.97 out of 5 average rating, 230 reviews

Apartment in Chestertown

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.

5 out of 5 average rating, 35 reviews

Water Views in Rock Hall

Brand new, custom built home featuring a wall of windows with water views of The Haven on Swan Creek. 3 bedrooms, 3 full baths. Enjoy the screened in porch, sunning yourself on the deck or warming up by the wood stove in the wintertime. Fun tile work in the bathrooms, a giant soaker tub, built in bunk beds (full size), rugs imported from Morocco & lots of original art, brings this home to life! This house is playful & has lots of personality. Walk or bike to all the marinas & eateries in town!

An aerial view showcases a quiet neighborhood with residential homes and proximity to the Chesapeake Bay. The large backyard is visible, along with a mix of greenery and pavements. Multiple marinas are located nearby, complementing the tranquil setting.

5 out of 5 average rating, 86 reviews

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

4.99 out of 5 average rating, 108 reviews

Cottage in Rock Hall

Cottage by the Bay in Rock Hall, MD

Sunny cottage in quiet waterside town of Rock Hall. Easy walk into downtown: grocery store, cafe, gift shop with beautiful housewares, gifts and jewelry, styling salon, quilt shop, ice cream shop, and local produce market. Gas fireplace, screened porch, stone patio, deck, several bicycles, tv for dvd's. Restaurants, crabs, Eastern Neck Wildlife Refuge, and nearby Tolchester and downtown Chestertown. Public pool, small beach (& picnic gazebos), bike around town...come to relax year round!

5 out of 5 average rating, 19 reviews

A patio area features a round table surrounded by six chairs, with colorful striped cushions. Nearby, a stone fire pit sits on a gravel surface, framed by lush green grass and a scenic view of the river, under a clear blue sky.

Home in Millington

Anchors Away

Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar experience and utilize the well-appointed kitchen. Unwind in the screened-in porch with a book and river views. Outdoors, the dock invites relaxation by the water. Gather around the wood fire pit for memorable nights under the stars. Enjoy Kayaks, fishing poles and family games! Anchors Away promises an unforgettable riverside retreat. We look forward to hosting you!

Guest suite in Chestertown

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.

4.99 out of 5 average rating, 221 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

5 out of 5 average rating, 29 reviews

The charming cottage features a covered front porch with a white railing and a decorative door, framed by lush greenery and blooming hydrangeas. A flag is displayed proudly, while stairs lead up to the welcoming entrance. Natural light brightens the overall exterior.

Cottage in Betterton

Charming Home w/Great Porch

We would love to share our well-loved cottage on the Bay with you. Most loved for its beautiful views and quiet town, it is a perfect place to relax with great beach access. We think you'll love it too. Plenty of space to spread out and comfy spaces to enjoy together: whether on the screened porch (our favorite), in the updated foodie-kitchen, or swinging on the swing, snoozing in hammock or walking to the beach - you will be glad you found this place-we definitely are!

5 out of 5 average rating, 16 reviews

Condo in Betterton

Beach Haven Hideout

We are a small enclave of condos, perched high on a bluff, overlooking the Chesapeake Bay. From the deck you have wonderful views of the beach and the best Bay sunsets! We are no more than 100 steps to the beach, where you have a picnic pavilion, beach volleyball, and BBQ area with communal grills and picnic tables. This is the perfect getaway for small families or couples.

4.86 out of 5 average rating, 57 reviews

A private in-ground pool is surrounded by lush greenery and vibrant pink flowers. Comfortable lounge chairs are positioned along the poolside, creating a relaxing atmosphere. A hot tub is located nearby, offering additional space for leisure and enjoyment.

Home in Millington

The Peaceful Getaway (with private pool & hot tub)

Kick back and relax at this charming peaceful getaway, the perfect place to enjoy with friends and family! This beautiful 2 story spacious house is back off a dead end road, but still only minutes from the main highway. It’s very private with a beautiful in ground pool and hot tub behind the house! And also lots of space for outdoor cooking. Please no pets

A large flowering tree with pink blossoms is prominently featured, casting a soft shade on the lush green lawn. Petals cover the ground beneath the tree, while a nearby fire hydrant adds a touch of color in the foreground.