Vacation rentals in Caroline County

4.9 out of 5 average rating, 87 reviews

A traditional nineteenth-century farmhouse is nestled among trees, showcasing white siding and dark shutters. The entrance is framed by greenery, providing a welcoming view. A spacious lawn surrounds the house, inviting outdoor activities and relaxation in a peaceful setting.

Home in Denton

Historic 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

4.93 out of 5 average rating, 76 reviews

An outdoor seating area features several dark wooden chairs arranged around a stone fire pit. Soft lighting reflects off the water feature, which includes layered rocks and greenery. The background showcases a landscaped yard with a wooden fence and a glimpse of the historic home.

Place to stay in Denton

Turnbridge Manor - Waterfront Historic House

JeffRating, 5 stars4 days ago

Great historic house with a restaurant/pub just down the street. Our group had plenty of room and the house was comfortable for our party of 6. Good place to stay if you have a day of crabbing or fishing nearby in the eastern shore. Super communicative and accommodating host and really was a no hassle check in when we arrived. Next time we have a charter in the area will book again!

4.95 out of 5 average rating, 98 reviews

A spacious two-story home is surrounded by manicured lawns and trees, set against a backdrop of the river. The exterior features a wooden facade, large windows, and a red railing along the porch, inviting a sense of openness and connection to nature.

Home in Preston

River House on the Choptank

SandyRating, 5 stars2 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!

Apartment in Greensboro

4.93 out of 5 average rating, 110 reviews

Awesome River House Waterfront Apartment

JenniferRating, 5 stars45 months ago

We have nothing but praise and gratitude for this lovely river hideaway in the woods after our weeklong restorative "working vacation" there. The apartment is cozy and comfortable, the surrounding area is beautiful, the hosts are lovely, and despite the feeling of privacy and "middle of nowhere" there are great stores, restaurants, area attractions, etc. all nearby. We loved drinking our morning coffee on the floating pier while watching the early morning mist (and chevrons of geese) rising from the river. We loved kayaking and swimming throughout the day from steps away from our apartment door. We loved being greeted by BIRDS BIRDS BIRDS in the nearby trees and feeders every time we stepped outside. And we absolutely loved sitting by the beautiful outdoor chiminea fire at night! We will be back. Thank you Helen, Peter, Sophie, and Moose!

5 out of 5 average rating, 37 reviews

Farm stay in Centreville

No Fees~Historic Lansdowne Manor

AndrewRating, 5 stars1 month 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.

4.85 out of 5 average rating, 148 reviews

A charming log home with a stone chimney is framed by lush greenery. The spacious front porch invites relaxation, and wooden railings enhance the rustic appeal. Natural elements are evident in the surrounding landscape, adding to the serene atmosphere of the lodge.

Cabin in Goldsboro

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

JanetRating, 5 stars3 days 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.

4.97 out of 5 average rating, 155 reviews

Home in Greensboro

Cozy Riverside Cottage in the Woods

ChuckRating, 5 stars1 month ago

Just a wonderful location. Very private and the property is beautiful. The house was well-equipped; it included a couple of kayaks that we used on the Choptank River, where we saw ospreys, eagles, and even a beaver. The beds were comfortable and the decor and other items in the house were very interesting. We likely will be back some time.

Vacation rentals for every style

Get the amount of space that is right for you

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Popular amenities for Caroline County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Caroline County

4.95 out of 5 average rating, 98 reviews

Home in Preston

River House on the Choptank

SandyRating, 5 stars2 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!

4.97 out of 5 average rating, 95 reviews

A serene wooded area is visible, featuring tall trees with expansive canopies. A small pond reflects the greenery, surrounded by lush grass. Sunlight filters through the leaves, creating a calm and inviting natural setting.

Home in Greensboro

Cozy 2 bedroom home on wooded private lane

BoRating, 5 stars2 weeks ago

Cindy's place was very relaxing with beautiful surroundings between farmland and forests.

4.9 out of 5 average rating, 87 reviews

Home in Denton

Historic 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

4.85 out of 5 average rating, 148 reviews

Cabin in Goldsboro

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

JanetRating, 5 stars3 days 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.

5 out of 5 average rating, 37 reviews

Farm stay in Centreville

No Fees~Historic Lansdowne Manor

AndrewRating, 5 stars1 month 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.

4.97 out of 5 average rating, 155 reviews

Home in Greensboro

Cozy Riverside Cottage in the Woods

ChuckRating, 5 stars1 month ago

Just a wonderful location. Very private and the property is beautiful. The house was well-equipped; it included a couple of kayaks that we used on the Choptank River, where we saw ospreys, eagles, and even a beaver. The beds were comfortable and the decor and other items in the house were very interesting. We likely will be back some time.

4.99 out of 5 average rating, 71 reviews

The entrance sign for Bay Country Cottage features a classic design with the name 'Bay Country Cottage' adorning a wooden background. A fish illustration is prominently displayed in the center of the sign, surrounded by a natural mulch landscape.

Home in Preston

Bay Country Cottage * Peaceful

JohnRating, 5 stars2 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.