Holiday houses in Caroline County

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Popular amenities for Caroline County holiday rentals

Other great holiday rentals in Caroline County

Guest favourite
Home in Preston
4.96 out of 5 average rating, 91 reviews

River House on the Choptank

LindaRating, 5 starstoday
This is our second time staying at Steven’s house. It is a perfect retreat for us.
Guest favourite
Home in Greensboro
4.96 out of 5 average rating, 85 reviews

Cozy 2 bedroom home on wooded private lane

CRating, 5 stars1 month 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 favourite
Home in Denton
4.9 out of 5 average rating, 87 reviews

Historic 19th Century Eastern Shore Farmhouse

PaulRating, 5 stars3 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
Cabin in Goldsboro
4.85 out of 5 average rating, 137 reviews

Wigwam Lodge~Hot Tub~MasterSuite~Woodland Views

ConstantinRating, 5 stars3 weeks ago
The location is ideal for a quiet retreat. The pictures don't do it justice. Worth mentioning that the hot tub is behind the house, NW corner, next to the patio, so there's easy, private, covered access to it from the house. Everything is organized very well inside, amenities are excellent, house is very well equipped, with two heating options available (wood and gas). Host was very communicative, responded to all our questions very quickly. Would definitely recommend for a quiet, comfortable log cabin destination.
Guest favourite
Home in Denton
4.96 out of 5 average rating, 23 reviews

*NEW* The Wilder Way

KarynRating, 5 stars1 month 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 favourite
Farm stay in Centreville
5 out of 5 average rating, 35 reviews

No Fees~Historic Lansdowne Manor

NicholasRating, 5 stars2 months ago
This place is a must stay for any hunters coming to the area to take advantage of the great waterfowl and deer season. I’ve been hunting in Centreville for over 10 years and will stay here every year moving forward if the property is available. My group loves to cook and the kitchen here is perfect to make (and eat) a large meal as a group. I couldn’t be happier with my stay and will be coming back again.
Guest favourite
Home in Queen Anne
4.98 out of 5 average rating, 57 reviews

Farmhouse w/hot tub, close to Tuckohoe State Park

MichaelRating, 5 stars2 weeks ago
Sarah is an amazing host with an awesome property. We loved the space and felt that everyone had enough room to come together and hang out but also enough space to spread out when we wanted our alone time. We will be renting from Sarah again she's the best!
Guest favourite
Home in Greensboro
4.97 out of 5 average rating, 150 reviews

Cozy Riverside Cottage in the Woods

Mary CRating, 5 stars3 months ago
Carrie’s house was beautiful, peaceful and everything we were looking for!!! We will definitely stay there again.