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Vacation rentals in Caroline County
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Top-rated vacation rentals in Caroline County
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Popular amenities for Caroline County vacation rentals
Other great vacation rentals in Caroline County
Superhost
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Home in Hurlock
4.6 out of 5 average rating, 15 reviewsOutdoor Paradise! Large house w/outdoor pavilion
ArikaRating, 5 stars5 months ago
Harold and Ashley were a peach to work with. Pleasure to stay in the home and most definitely would revisit if applicable.
Guest favorite
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Home in Preston
4.96 out of 5 average rating, 90 reviewsRiver House on the Choptank
JasonRating, 5 stars1 month ago
Leaving 5 stars because the place overall was great! There were only 2 drawbacks. The first is that the bathroom setup was a bit odd. There’s one bathroom downstairs, with one door to a bedroom and another door to the kitchen, good enough. But upstairs, there’s 3 bedrooms and 1 bathroom which is smack in between two of those bedrooms with doors to each of them *but no door to the hallway*. This means that if you’re sleeping in the 3rd bedroom upstairs, the largest one, you either have to walk through someone’s bedroom upstairs to get to the bathroom or walk all the way downstairs to get to the bathroom. Again, a bit odd, but not a huge deal. Second thing is that some lights/fans didn’t work, one of the bedrooms the light switch didn’t work at all for the ceiling fan light, and there was no string to pull for it either. This was okay though because we really only used the bedrooms at night to sleep and there was a lamp that worked. So overall we enjoyed the place and would recommend!
Guest favorite
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Home in Greensboro
4.96 out of 5 average rating, 85 reviewsCozy 2 bedroom home on wooded private lane
CRating, 5 stars2 weeks ago
This was a fantastic place in numerous regards. Was private and secluded. Place was pristine and very well taken care of. Cindy included several items that most B&B’s do not. Fresh coffee beans, condiments in fridge, lots of extra paper products. Place was very modern as well, and had very very comfortable bedding. Cindy was very quick to respond to all our questions prior to stay and during stay. Would we return again? We are already planning our next trip.
Guest favorite
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Home in Denton
4.9 out of 5 average rating, 87 reviewsHistoric 19th Century Eastern Shore Farmhouse
PaulRating, 5 stars2 months ago
This historic property in Maryland is an amazing find. The property is a lovely two plus acres with many cozy retreats to stop and take in the wonderful trees. If you want a more rigorous outdoor experience, there is a lovely park 5 minutes away and a larger area with an arboretum about 15 minutes away. It is an easy walk into downtown which has several restaurants. The hosts have thought of everything, and I do mean everything. The character of the house is exceptional, but it is comfortable not stuffy. Lots of amazing artwork and books throughout. The kitchen is fully stocked and comfortable to eat or cook in. The rain shower in the bathroom was delightful and the beds are comfortable. It was a perfect place to have a mini family reunion for a few days. We will be visiting the house again
Superhost
![](https://a0.muscache.com/im/pictures/2360bf6d-179b-40ae-9486-bb94e382548f.jpg)
Cabin in Goldsboro
4.84 out of 5 average rating, 135 reviewsWigwam Lodge~Hot Tub~MasterSuite~Woodland Views
ChrisRating, 5 stars2 weeks ago
Melody was very kind and responsive. The house was beautiful and clean. Definitely would come back!
Guest favorite
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Home in Denton
4.96 out of 5 average rating, 23 reviews*NEW* The Wilder Way
KarynRating, 5 stars2 weeks ago
We stayed in January 2025 for a family gathering with 6 adults and 6 kids (ages 5 months to 8 years). The house is lovely and we enjoyed cooking in the beautiful kitchen and sitting by the fireplace. Although the yard and play structure were covered in snow, the kids enjoyed it all anyway including roller skating and scootering on the long driveway. Our host was very responsive to a few issues we encountered. Something to know about the bunk room--you must go through the garage to get to it. It was fine for our purposes. The beds and linens were all very comfortable. The shower and bath in the primary bedroom was a treat.
Guest favorite
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Farm stay in Centreville
5 out of 5 average rating, 34 reviewsNo Fees~Historic Lansdowne Manor
AlfiaRating, 5 stars2 months ago
As a New Yorker, I would say that we are KNOWN for doing too much and of course I did not disappoint. I decided to coordinate a remote Birthday/ Thanksgiving Dinner in Camden, Delaware. Everything at this location was great for MY purpose! There were 6 of us in total & a family dog. No human or dog was displaced. Everyone had there own bed full, queen or king and there was a single bed as a spare! There were 3, clean, functioning bathrooms. The water was nice and hot! I was able to controll my own temperature. There were zones for the units, whereas under used areas did not necessarily require much heat. There was functioning washer/dryer setup, both, stand-alone. Detergent & Dryer sheets were provided. I booked this place because the kitchen stood out to me! There were 3 of us cleaning 10lbs of chicken, very comfortably. I was able to prep potatoe salad, Deviled eggs, Cheddar bay biscuits, 2 pans of ziti, Cupcakes, brownies, etc. Arriving at night was a little creepy!
Guest favorite
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Home in Greensboro
4.97 out of 5 average rating, 150 reviewsCozy Riverside Cottage in the Woods
Mary CRating, 5 stars2 months ago
Carrie’s house was beautiful, peaceful and everything we were looking for!!! We will definitely stay there again.
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