
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
Top guest favourite

Farm stay in Denton
5 out of 5 average rating, 16 reviewsLyford Landing Farmhouse
AnnRating, 5 stars1 month ago
Jim’s place was a cozy cabin that felt very private, and yet a quick drive to Denton, St. Michael’s, Easton and Oxford, where gorgeous scenery, restaurants and shopping abound. Jim offered us a possible solution to a transportation, was present when I arrived and offered assistance in unloading my car, and gave me a delightful tour of the property and a quick history lesson about the property. He also introduced me to a close neighbor in case we needed anything. A wonderful host! I will be back.
Guest favourite

Home in Preston
4.95 out of 5 average rating, 98 reviewsRiver House on the Choptank
SandyRating, 5 stars3 weeks ago
The house was perfect for us. We were in town for grandson's graduation and needed extra space and this definitely delivered. The property was amazing. Even though we couldn't physically enjoy much outside activities due to the rain we did get to enjoy beautiful views of the river from the large picture windows. Steven was always quick to respond to messages which was much appreciated!
Top guest favourite

Home in Greensboro
4.97 out of 5 average rating, 96 reviewsCozy 2 bedroom home on wooded private lane
AnnaRating, 5 stars1 day ago
Cindy is a great host. One of the best! The house is very comfortable with all amenities.
Superhost

Home in Denton
4.9 out of 5 average rating, 88 reviewsHistoric 19th Century Eastern Shore Farmhouse
PaulRating, 5 stars6 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, 148 reviewsWigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views
JanetRating, 5 stars1 week ago
Enjoyed our stay in this lovely cabin. It was an excellent base to go to Bethany Bay, Cape May and even Philadelphia. The hot tub was amazing. Beds were very comfortable. Kitchen had everything we needed. Thank you for sharing your home with us.
Top guest favourite

Farm stay in Centreville
5 out of 5 average rating, 37 reviewsNo Fees~Historic Lansdowne Manor
AndrewRating, 5 stars2 months 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, 156 reviewsCozy Riverside Cottage in the Woods
Jeannine JBRating, 5 stars1 week ago
A wonderful place to Get-away, have a working vacay, appreciate the outdoors. It's quiet and rests the eyes. Our family agreed that this home is like a ski chalet not on a mountain but rather in Miniature America Maryland on a river. Would love to return.
Top guest favourite

Home in Preston
4.99 out of 5 average rating, 71 reviewsBay Country Cottage * Peaceful
JohnRating, 5 stars6 days ago
The wifi either didn't work or was intermittent. Thus the streaming services for the TV would not connect. I prefer standard network stations plus CNN, Fox and ESPN. Those were not available on this setup.
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- Broadkill Beach
- Fortescue Beach
- Betterton Beach
- Oriole Park at Camden Yards
- Higbee Beach
- M&T Bank Stadium
- Sandy Point State Park
- Dewey Beach Access
- Cape Henlopen State Park
- Patterson Park
- Willow Creek Winery & Farm
- Towers Beach
- Poodle Beach
- Delaware Seashore State Park
- Pearl Beach
- Quiet Waters Park
- Crystal Beach Manor, Earleville, MD
- Maryland Renaissance Festival
- Peninsula Golf & Country Club
- Flounder Pavilion Beach Front - Sandy Point State Park
- Heritage Shores
- Killens Pond State Park
- Plantation Lakes Golf and Country Club
- Lums Pond State Park