Holiday rentals in Caroline County

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.

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.

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.

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.

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.

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!

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.

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 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.