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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Top 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

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

ValueFamilyNearby

4.95 out of 5 average rating, 103 reviews

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

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.

ValueLocationIndoor spaces

5.0 out of 5 average rating, 45 reviews

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

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 2 kayaks, 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.

LocationFamilyOutdoor spaces

4.93 out of 5 average rating, 128 reviews

Top guest favorite

Home in Ridgely

Comfy Ridgely Home|Near Easton, DE, and Tuckahoe

Welcome to The Ridgely House. An Eastern Shore Escape! Enjoy small-town charm in this newly renovated 3-bedroom home. Enjoy easy self check-in via smart lock. Sip your morning coffee on the front porch, gather around the patio table in the spacious backyard, or unwind in our comfortable living spaces. Located minutes from the Delaware state line, 5 minutes from Tuckahoe State Park, 25 minutes from Easton, and within easy reach of St. Michaels, Annapolis, Blackwater Refuge, and the beach.

LocationFamilyGetting around

4.91 out of 5 average rating, 11 reviews

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

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.

LocationFamilyBathroom

4.93 out of 5 average rating, 110 reviews

Home in Preston

The Hatting Homestead

Escape to your private Eastern Shore retreat! Open 3BR/2BA home on 3 fenced acres, sleeps 12, with no pet limits. Very comfortable & supportive furniture and beds. Perfect for families, hunting & fishing groups. Parking for boats and trailers. Minutes from premier deer & waterfowl hunting, fishing, the Choptank River, and boat launches. Easy drives to Ocean City, Assateague, Baltimore & DC. Space, privacy, and adventure await. Fast Wi-Fi, peaceful country views, and unforgettable sunsets!

FamilyLocationBackyard

5.0 out of 5 average rating, 3 reviews

Top guest favorite

Farm stay in Greensboro

Frosty Acres Choptank River Farm

Bring your family for a memorable stay on our family waterfront farm, "Frosty Acres." Located on Maryland's Eastern Shore between Greensboro and Ridgely, this 3 bedroom/2 bath Victorian house on 60 waterfront acres surrounded by barns, fields, woods & farmland, once occupied by Choptank River Native Indians! Walk the trails and dirt roads that will take you through the farm to the campground area where you can launch your own boat, BBQ, kayak, fish, swim, have a campfire and tent camp.

LocationFamilySleep quality

5.0 out of 5 average rating, 13 reviews

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

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.

LocationFamilyAccess

4.97 out of 5 average rating, 145 reviews

Guest favorite

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

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.

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 14 reviews

Top guest favorite

Home in Centreville

Family Retreat at Historic Lansdowne Manor

Escape to Lansdowne, a historic Federal-period manor house recognized by the Library of Congress. This private, tranquil retreat offers a unique blend of vintage charm and modern comfort for up to 8 guests. Surrounded by open fields and nature, this 4 bedroom home features a fully equipped kitchen and high-speed Wi-Fi. Perfect for families and history lovers seeking a peaceful getaway just minutes from Centreville and a state park lake and trails.

FamilyValueSleep quality

5.0 out of 5 average rating, 63 reviews

Top 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

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.

ValueLocationGetting around

4.94 out of 5 average rating, 109 reviews

Superhost

The master suite features wooden beams and log walls, creating a rustic atmosphere. A plush bed is positioned next to a classic bench. Soft lighting illuminates the space, while a colorful woven rug adds warmth to the wooden floor.

Cabin in Goldsboro

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

Wigwam Lodge is an experience nestled in a pine & hard wood forest with rural privacy. Incredibly spacious decks. Surround Forest Views inside and out! 5-min from Choptank river, 20-min from Historic Denton, Irish Pub & Grocery, 1hr from the beach. Easy PARKING 10ft from the front door. Solid WIFI! Click “Show More” Below to SEE ALL Deets...

ValueFamilyComfort

4.86 out of 5 average rating, 182 reviews