Vacation rentals with beach access in Kent County

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Top-rated beach access rentals in Kent County

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Guest favorite

Home in Rock Hall

4.98 out of 5 average rating, 47 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

Guest favorite

Rental unit in Rock Hall

4.95 out of 5 average rating, 22 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

Cottage in Betterton

4.83 out of 5 average rating, 69 reviews

Cottage By the Chesapeake

This cozy cottage on the Eastern Shore of Maryland sits on a spacious private lot a five minute walk to Betterton Beach! Relax on the screened-in porch or fully-furnished living room after a day in the woods, or cook a homemade dinner in our fully-equipped kitchen. The community of Betterton offers tennis courts, covered outside picnic tables with grills, a brand new playground, and of course...THE BEACH! For a change of pace or a night out, Chestertown, Maryland is only a short drive away.

Guest favorite

Cabin in Chestertown

4.98 out of 5 average rating, 231 reviews

Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

Guest favorite

Cottage in Rock Hall

4.99 out of 5 average rating, 108 reviews

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!

Guest favorite

Rental unit in Worton

4.97 out of 5 average rating, 30 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.

Guest favorite

Home in Chestertown

5 out of 5 average rating, 10 reviews

Holiday Escape to the Riverside

Relax with the whole family or a big group at peaceful river home. Huge waterfront property. Bedroom, dining and living room views. River and tidal beach access. Kayak, SUP or canoe. Enjoy backyard games, outdoor dining, hammock or fire pit. Massive waterfront screened-in porch with 2 group dining and 2 seating areas. 10 min walk to adorable historic downtown. Festivals, art galleries, bakeries, ice cream, shops, spa & playground. This is our happy place - we hope it becomes yours!

Guest favorite

Home in Rock Hall

4.98 out of 5 average rating, 50 reviews

Private Chesapeake Bay Retreat w/ Bay Views!

Step into a relaxing retreat at this picturesque vacation rental on Chesapeake Bay! Complete with 2 bedrooms and 2 bathrooms, this spacious home offers a cozy fireplace and a stunning deck overlooking the water — perfect for enjoying the sunset! Explore the nearby Eastern Neck National Wildlife Refuge or take a scenic drive to the quaint shops and seafood restaurants in town. Whether you're seeking outdoor adventures or a peaceful coastal getaway, you’ll love this Rock Hall property!

Guest favorite

Home in Betterton

5 out of 5 average rating, 35 reviews

Ruby's Sea Glass Cottage near Betterton Beach

Have fun with the whole family at this stylish place in the center of Betterton, MD. You can walk to the beach to relax, find some sea glass or watch the sunset! There is a public park close to the cottage with a playground, tennis, pickle ball and basketball courts. This house has an adorable kitchen stocked with basic condiments. There are three tranquil bedrooms, one amazing bathroom and three beautiful outdoor spaces to unwind. Kids items upon request.

Guest favorite

Serviced apartment in Rock Hall

4.96 out of 5 average rating, 52 reviews

Bayside bungalow cottage by the sea

This quaint Cottage is located on a quiet residential road with quick access to the water. Located in Rock Hall, Maryland, guests will enjoy a getaway from the hustle and bustle of major cities. The Cottage boasts 1 bedroom and 1 bathroom, equipped with a private sauna. Guests are guaranteed to have a relaxing stay here at the Cottage House! Great views of Swan Creek and the Cheseapeake Bay.

Guest favorite

Home in Rock Hall

4.84 out of 5 average rating, 127 reviews

Pirates Perch

Rock Hall's most convenient vacation rental. Right on the parade route and walking distance to shops, ice cream, coffee, groceries and more! Sleeps 8 with 2 full baths. The master bedroom with full bath is on the 1st floor. Kitchen, dining room and living room. 3 TVs with WiFi internet. Off street parking for 3 full size vehicles.

Guest favorite

Home in Rock Hall

4.97 out of 5 average rating, 35 reviews

Eastern Shore Escape in the Heart of Rock Hall

Beautiful and cozy 3 bedroom (one queen, two kings (added this year!)), 2 bathroom home centrally located in the historic district of Rock Hall. The house is half a block from Main Street and an easy walk to shops and restaurants. Enjoy all that Rock Hall has to offer from delicious crabs to beautiful bay views. Nice people live here!