Holiday houses in Caroline County

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Top-rated holiday rentals in Caroline County

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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, 88 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

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, 109 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.

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

4.81 out of 5 average rating, 16 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, 48 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

4.96 out of 5 average rating, 112 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.

Top Guest favourite

A living area is featured, highlighted by a red sectional sofa and two brown armchairs. A small round table sits between the chairs, complemented by large windows adorned with orange curtains. A cozy black rug covers the floor, adding warmth to the space.

Home in Denton

5 out of 5 average rating, 8 reviews

Welcome to Harmony House!

Welcome to our cute, tiny but mighty home that offers a convenient location with just the perfect amount of space to relax and recharge. Each of the three bedrooms comes with a Nectar mattress and plenty of comfortable options for sleeping, along with storage for your items and luggage. The walk-in shower and complete kitchen will allow you to bring comforts from home and the lightning fast wi-fi signal keeps you connected during your stay. Convenient access to Highway 404.

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, 5 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, 88 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 favourite

An aerial view of a spacious red farmhouse surrounded by lush greenery and open fields. A saltwater pool is visible in the backyard, complemented by a patio area. The landscape includes manicured lawns and trees, creating a serene rural setting.

Home in Queen Anne

4.99 out of 5 average rating, 82 reviews

Farmhouse w/hot tub, close to Tuckohoe State Park

If you’re looking for a place to get away from the busyness of life, this is the place to go! Our newly furnished 7 bedroom farmhouse is perfect to bring your family or friends. The farmhouse sets on 2.5 acres, with woodland and open fields all around. It really feels like you’re in the middle of nowhere:) We promise you’ll leave feeling refreshed and rejuvenated!

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

4.85 out of 5 average rating, 160 reviews

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...