Vacation rentals in Caroline County

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Top-rated vacation rentals in Caroline County

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

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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

4.88 out of 5 average rating, 89 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 living room is defined by a large flat-screen television mounted on the wall. Comfortable seating includes two dark sofas and an armchair, arranged around a coffee table. Natural light enters through two wide windows, enhancing the warm ambiance of the space.

Home in Federalsburg

5 out of 5 average rating, 14 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

A stately historic home is depicted from the front, showcasing a charming design with white siding and a blue front door. The property features a peaked roof and is surrounded by lush greenery, including several trees and well-maintained shrubs.

Place to stay in Denton

4.94 out of 5 average rating, 78 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

Superhost

A charming country house is nestled among mature trees, featuring a well-maintained lawn. The exterior showcases a mix of brick and neutral siding, with large windows and a covered porch. A gravel driveway leads to the entrance, complemented by decorative landscaping in the front yard.

Home in Hurlock

4.67 out of 5 average rating, 18 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 charming Cape Cod house features a blue exterior with white trim and a welcoming front door. Large windows allow natural light to illuminate the entryway. A small set of wooden steps leads up to the entrance, flanked by low greenery and a grass lawn.

Farm stay in Denton

5 out of 5 average rating, 17 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 bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.

Home in Preston

4.95 out of 5 average rating, 99 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

The exterior view showcases the townhouse entrance, featuring a dark blue door framed by white trim. Two windows on either side are adorned with dark shutters. A small welcome mat lies on the concrete step, with neatly trimmed landscaping in the foreground.

Home in Denton

4.93 out of 5 average rating, 130 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.

Two dogs, a yellow Labrador and a black poodle, are standing on a wooden dock overlooking a serene river. Lush green trees provide a natural backdrop, while a canoe is visible nearby. The scene captures a peaceful moment by the water.

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.

A seasonal heated pool is surrounded by lush greenery, with comfortable lounge chairs positioned nearby. The pool's clear water reflects the blue sky, creating a serene atmosphere. A fenced area enhances privacy, and a gathering space is visible under the shade of trees.

Home in Denton

4.9 out of 5 average rating, 10 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 single-story home is set amidst a lush, green lawn, surrounded by trees and natural vegetation. The exterior features a light-colored facade with a welcoming front entry and flower beds to the sides, enhancing the serene atmosphere of the wooded location.

Home in Greensboro

4.97 out of 5 average rating, 100 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.

The entryway features a natural wood door with multiple glass panes, framed by black trim. A decorative lantern is positioned beside the door. A lush green fern is presented in a dark planter next to a striped welcome mat.

Home in Denton

New place to stay

The Last Hurrah Farmhouse

1875 renovated, 2-bedroom farmhouse. The cozy bedrooms offer a comfortable queen bed, 2 full beds, 2 twin beds for a tranquil night's sleep. 2 full and 1 1/2 bath ensure convenience for all. Our organic farm has horses, chickens, rabbits, dogs, cats. None of which have access to this property but nice watching them all live their best lives on our farm. This ensures the quiet you are looking for. We’re happy to suggest local spots to make your stay more enjoyable.

Guest favorite

A single-family home with a brick exterior is surrounded by greenery. The inviting front porch is complemented by a stone pathway leading to a spacious outdoor seating area, featuring a fire pit and chairs for relaxation.

Bungalow in Queen Anne

4.95 out of 5 average rating, 76 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.