
Holiday rentals in Caroline County
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Top-rated holiday rentals in Caroline County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Caroline County
Guest favourite

Home in Preston
4.96 out of 5 average rating, 93 reviewsRiver House on the Choptank
MichelleRating, 5 stars3 weeks ago
We really enjoyed our stay at Steven’s River house on the Choptank River. I appreciated the beautiful, peaceful atmosphere while sitting on the back deck! The home is clean, open and very comfortable. Steven was always quick to answer emails and we would love to stay again should we come back to the area!
Top guest favourite

Home in Greensboro
4.97 out of 5 average rating, 89 reviewsCozy 2 bedroom home on wooded private lane
Stan And JenRating, 5 stars5 days ago
We walked in and felt at home. The space is open and bright with great nature views front and back. Every possible amenity is provided from gorgeous homemade quilts, many towels and pillows, to abundant paper products. Kitchen has everything (I have serious sink envy over that huge farmhouse stainless steel sink!). We spent a lot of time in the living room in the morning and the sunroom in the afternoon sun. Where ever you look, you have birds, deer, wild turkey and even the resident ground hog. At bedtime, you are in for a treat with the comfy mattresses, soft linens and did I mention the quilts? Not only are they art in and of themselves but snuggling up in one is luxury! The ambiance is excellent but what made our stay gold star worthy was our hosts- so easy to work with on check in/out, they made the time to personally do a meet and greet with us and- upon request we got to spend time with Burton the cat! They personify why Airbnb stays are bridges to meeting new friends.
Superhost

Home in Denton
4.9 out of 5 average rating, 87 reviewsHistoric 19th Century Eastern Shore Farmhouse
PaulRating, 5 stars4 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, 145 reviewsWigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views
TomRating, 5 stars6 days ago
Loved the cabin! Especially enjoyed the hot tub and board games and super comfortable beds! Woke up every morning to the sounds of the birds. Perfectly clean, quiet and peaceful (we did think it would be set back further from the street, but there’s almost no traffic so the road noise was minimal). The wood-fired hot water and heat give a nice rustic touch, plenty of wood is included and it only needs to be stoked twice a day. Laundry soap is provided, which was a nice bonus, as are the kitchen staples (peanut butter, flour, spices, popcorn, etc). Melody is a great communicator, answering all questions promptly, and everything was as described in the listing. Everything is labeled and the instructions and house rules are clear and easy to understand. As someone who travels frequently, this property is well above average, particularly in this region. Will happily stay here again next time we’re in the area!
Top guest favourite

Farm stay in Centreville
5 out of 5 average rating, 36 reviewsNo Fees~Historic Lansdowne Manor
AndrewRating, 5 stars4 days ago
I had a wonderful stay at the Manor. Alex was an exceptional host—very responsive and accommodating throughout my visit. The manor is beautiful, featuring a charming vintage appeal perfectly complemented by modern amenities. It felt both timeless and comfortable. Conveniently, grocery stores and restaurants are just a short drive away, which made my stay even more enjoyable. Overall, it was a fantastic experience, and I would love to stay again.
Top guest favourite

Home in Greensboro
4.97 out of 5 average rating, 152 reviewsCozy Riverside Cottage in the Woods
WinstonRating, 5 stars2 weeks ago
I cannot recommend this listing enough! As described, the house was deep in the woods and right on the river, providing a secluded, peaceful stay. We had direct access to the water, and while we did not go into the water, we enjoyed watching the local wildlife from the pier. The home itself was well furnished and amazingly stocked. Everything was clean, and there was an abundance of conveniences available. The kitchen, in particular, was very well supplied. The beds and furniture were comfortable and spacious for our group of five. The HVAC kept the house the perfect temperature our entire stay. There were several amenities that we ended up not using, but were glad to have them available, such as the fire pit, fire place, kayaks, and grill. We wanted for nothing! Carrie was an amazing host, answering all of our questions and ensuring that we had an amazing trip. You won't go wrong booking with Carrie!
Top guest favourite

Home in Preston
4.98 out of 5 average rating, 65 reviewsBay Country Cottage
YasmineRating, 5 stars5 days ago
definitely will return great beautiful house great place to stay

Home in Preston
4.44 out of 5 average rating, 27 reviewsLITTLE CREEK HIDEAWAY
ShawnRating, 5 stars14 months ago
Our second time staying, we will stay here again!
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- Miami Beach
- Sandy Point State Park
- Dewey Beach Access
- Big Stone Beach
- Patterson Park
- Oriole Park at Camden Yards
- Heritage Shores
- Six Flags America
- Cape Henlopen State Park
- Delaware Seashore State Park
- Killens Pond State Park
- M&T Bank Stadium
- Gerry Boyle Park
- Willow Creek Winery & Farm
- Towers Beach
- Quiet Waters Park
- Maryland Renaissance Festival
- Bulle Rock Golf Course
- Crystal Beach Manor, Earleville, MD
- Poodle Beach
- Plantation Lakes Golf and Country Club
- Peninsula Golf & Country Club
- Idlewilde Restoration Project
- Quiet Waters Dog Beach