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 favourite

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, 21 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.

Top guest favourite

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, 84 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

The Victorian house is situated on a well-maintained lawn, featuring manicured shrubs and an American flag planted prominently in front. Lush trees provide shade in the background, while a clear blue sky with white clouds adds to the inviting landscape.

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 outside of Greensboro and Ridgely the 3 bed/2 bath Victorian house sits 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 up to 25 ft, BBQ, kayak, fish, swim and tent camp by the fire.

Guest favourite

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

4.93 out of 5 average rating, 107 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 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.

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

4.68 out of 5 average rating, 19 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.

Guest favourite

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, 20 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.

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

4.8 out of 5 average rating, 15 reviews

Riverfront Denton Estate on 7 Acres w/ Heated Pool

Dog Friendly w/ Fee | Private Deck | 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 favourite

Home in Centreville

5 out of 5 average rating, 47 reviews

Lansdowne Manor | Firepit | BBQ | Pets | 198 Mbps

Historic country manor located in a private tranquil setting, surrounded by mature trees & nature. ★ "An absolutely amazing property—graceful, historical, and very well cared for." ☞ Deck w/ BBQ + fire pit + dining ☞ Spacious backyard w/ lush views ☞ Fully equipped + stocked kitchen ☞ Parking → driveway (4 cars) ☞ Onsite washer + dryer ☞ 55” + 43” smart TVs ☞ 198 Mbps wifi ☞ Pet friendly 9 mins → DT Centreville (cafes, dining, shopping) 13 mins → Tuckahoe State Park hiking trails

Top guest favourite

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, 105 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

5 out of 5 average rating, 4 reviews

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 favourite

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

4.94 out of 5 average rating, 84 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.