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, 8 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 serene view of the Choptank River is captured, with two lounge chairs positioned on a wooden deck. Lush green grass surrounds the deck, while trees and gentle ripples in the water reflect the calm atmosphere. A distant dock structure is visible across the river.

Place to stay in Denton

4.93 out of 5 average rating, 71 reviews

Turnbridge Manor - water Front 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

A wooden dock extends over a calm river, surrounded by lush green trees. The clear blue sky and scattered clouds reflect softly on the water's surface, creating a serene atmosphere. Natural vegetation frames the scene, enhancing the peaceful environment.

Home in Preston

4.44 out of 5 average rating, 27 reviews

LITTLE CREEK HIDEAWAY

Relax at Little Creek Hideaway, perfect family getaway during any season. 10 mins from Easton, property will make you feel like you're miles away from life's hustle and bustle. Two kayaks , outdoor fire-pit. Stocked kitchen, dining room with seating for 6, game room with ping pong table, sunny family room with a fireplace and flat screen TV. Airbnb does not collect pet (s) fee... we have a pet fee of $100 that must be paid at check-in. Pet rules must be followed or extra charge will apply.

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

Home in Preston

4.96 out of 5 average rating, 94 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, 122 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.

A serene winter landscape showcases a wooden dock extending into a frozen river. Bare trees line the riverbank, and a rustic home is visible in the background. Clear blue skies add a bright contrast to the quiet scene.

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

4.89 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 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, 89 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, 36 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.