Vacation rentals in Caroline County

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Top-rated vacation rentals in Caroline County

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Superhost

A traditional nineteenth-century farmhouse is nestled among trees, showcasing white siding and dark shutters. The entrance is framed by greenery, providing a welcoming view. A spacious lawn surrounds the house, inviting outdoor activities and relaxation in a peaceful setting.

Home in Denton

4.9 out of 5 average rating, 87 reviews

Historic 19th Century Eastern Shore Farmhouse

Nineteenth-century farmhouse with barn and corn crib on 2.25 acres in Denton, Maryland. The house has thirteen rooms including four bedrooms, (one is a child's room), a sunporch, an office, eat-in kitchen, and three bathrooms. The kitchen is fully stocked with a blender, KitchenAid mixer, microwave, convection oven/toaster, and coffee maker. We also have games (children's and adults), a tv for streaming, Wi-fi, and books. The property has benches and pathways. Rooms are on multiple levels.

Top guest favorite

A spacious sunroom is enclosed with screens and features a comfortable seating area furnished with dark wicker furniture and grey cushions. A glass-top coffee table is positioned in the center, complemented by a decorative pillow. Natural light floods the area, creating a bright and inviting space.

Home in Federalsburg

5 out of 5 average rating, 12 reviews

Welcome to the Cornfield!

Conveniently located right off highway 404 outside of Denton this spacious 3 bedroom modular home is ready to welcome you. Electric car charger, Nectar mattresses, filtered water, a dedicated fiber connection and 2 large televisions are some of the amenities to enjoy. Centrally located in Caroline County, this home is 20 minutes to Seaford or Harrington, 30 minutes to Easton and around an hour to Rehoboth Beach. Pet friendly home on a couple acres with convenient access to Martinak and Tuckahoe.

Guest favorite

Place to stay in Denton

4.93 out of 5 average rating, 73 reviews

Turnbridge Manor - Waterfront Historic House

A waterfront property located in the heart of downtown Denton, on Maryland's Eastern Shore, the stately historic home built in the 1860’s offers modern amenities and luxurious accommodations. Guests can take in the charm of Denton from our sunny front porch or sit in the many outdoor oases to relax and enjoy the beautiful terraced grounds overlooking the tranquil Choptank River. Located less than 60 minutes to the beach, 35 minutes to historic St. Michaels and minutes to the Harriet Tubman Byway

Home in Hurlock

4.6 out of 5 average rating, 15 reviews

Outdoor Paradise! Large house w/outdoor pavilion

Large Country house secluded on 7.5 acres. Appreciated for historical charm and modern updates. Stocked pond on property with large outdoor pavilion for entertaining. House is a spacious layout with room for everyone! Fenced in backyard for the pets and play set for kids. Large soaking tub in the master bathroom to help you relax and watch Netflix and chill after a long day of enjoying the local historical attractions. A Tesla charger on site and 50amp hook up for other EV’s or camper hook up.

Top guest favorite

A Cape Cod house is set amidst green grass and shaded by a large tree. Lounge chairs in a vibrant hue are arranged on the lawn, with steps leading up to the entrance. A garden shed is visible nearby, complementing the rural landscape.

Farm stay in Denton

5 out of 5 average rating, 16 reviews

Lyford Landing Farmhouse

Enjoy the fresh country air and peace and quiet. Located between Denton and Easton but set back from the road amidst farm fields and abutting the Choptank River, Lyford Farm is a good location to rest while enjoying day trips to the surrounding towns. Nearby boat launches offer access to the Choptank and Tuckahoe Rivers for fishing or pleasure boating. Bring your boat with you their is plenty of open area to park it You will be able to disconnect from the daily grind and enjoy birdwatching.

Guest favorite

A spacious two-story home is surrounded by manicured lawns and trees, set against a backdrop of the river. The exterior features a wooden facade, large windows, and a red railing along the porch, inviting a sense of openness and connection to nature.

Home in Preston

4.96 out of 5 average rating, 95 reviews

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or kayak, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Guest favorite

Home in Denton

4.94 out of 5 average rating, 123 reviews

Mallard Landing Townhouse

Welcome to Maryland’s Eastern Shore and your own private townhouse in a quiet and peaceful neighborhood. You’ll be conveniently located less than an hour to the beaches, with short travel to Easton, Dover, D.C. and Baltimore. But why bother traveling when your in the beautiful historic town of Denton and all it has to offer with many up and coming stores, restaurants, and many other sights to enjoy including the Choptank River, Martinak State Park, Tuckahoe State Park, and historic downtown.

Apartment in Greensboro

4.93 out of 5 average rating, 110 reviews

Awesome River House Waterfront Apartment

Having been called "a treehouse on the river" by many guests since there is a oneness with nature afforded by the design of our home. The ever-changing view of the river is always enchanting as is the ebb & flow of the tide on the Choptank River. Our dock provides excellent river access and is only 20 feet from the house and has a new (2020) floating dock that affords easy access for swimming and kayaking. A canoe and kayaks are available for guest use and there are amazing sunsets as well.

The exterior of a two-story white house is highlighted, featuring a large front porch with comfortable seating. Lush greenery is visible in the foreground, and the welcoming entryway is adorned with a central light fixture. Two sets of double doors provide access to the home.

Home in Denton

4.89 out of 5 average rating, 9 reviews

Riverfront Denton Estate on 7 Acres w/ Fire Pit!

Dog Friendly w/ Fee | Private Dock | Pool Table Spend your next Maryland getaway staying in style at a former Governor's family home. Located on a beautiful 7-acre plot of land along the Choptank River, this stunning Denton vacation rental is a perfect hidden gem for an exciting family retreat. Take the provided kayaks out on the water, or check out the driving range next door before heading back to this luxurious 5-bedroom, 3.5-bathroom house to unwind around the wood-burning fire pit!

Top guest favorite

A serene wooded area is visible, featuring tall trees with expansive canopies. A small pond reflects the greenery, surrounded by lush grass. Sunlight filters through the leaves, creating a calm and inviting natural setting.

Home in Greensboro

4.97 out of 5 average rating, 92 reviews

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

Guest favorite

An inviting outdoor space features a circular arrangement of four adirondack chairs surrounding a central fire pit. Warm lighting hangs above, creating a cozy ambiance. The gravel surface is complemented by landscaping elements, while a backdrop of wooden fencing enhances the secluded feel.

Bungalow in Queen Anne

4.94 out of 5 average rating, 72 reviews

Private bungalow with fire pit near Easton, Denton

- High-speed Internet - Premium Samsung washer and dryer - Fire Pit - Level 2 EV Charger - Two (2) cruiser bicycles - Memory foam mattresses - Full kitchen - Smart TV - Quiet, secluded space with easy access - 5 minutes to Denton - 15 minutes to Easton - 15 minutes to Centreville - 30 minutes to St. Michaels Located just minutes from both Easton and Tuckahoe State Park, you'll have endless opportunities for outdoor adventure.

Top guest favorite

Farm stay in Centreville

5 out of 5 average rating, 37 reviews

No Fees~Historic Lansdowne Manor

Welcome to Lansdowne Manor, some of the best preserved history of the late 18th/early 19th century on the Eastern Shore. Partially restored and tastefully amended, this historic home is superbly utilitarian. The grand double parlors can be used for small dinner parties or quiet Netflix nights. Situated on 19 acres, enjoy unmatched privacy and tranquility. Sleeps up to 8.