A river with a green embankment and a boat.

Vacation Rentals in Caroline County

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Our top choices for Caroline County vacation rentals

A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

1. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
United States
Jessica H.
The price is ￥56,887
￥96,313 total
includes taxes & fees
Oct 27 - Oct 28
Turnbridge Manor
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is ￥15,644
￥25,100 total
includes taxes & fees
Oct 20 - Oct 21
First Floor Studio Apartment in Historic Chestertown
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

3. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (29 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is ￥10,745
￥19,765 total
includes taxes & fees
Oct 20 - Oct 21
Guest Suite for up to 2 in a Victorian on the Chester River
A bedroom with a bunk bed, a single bed, a desk, and a chair.

4. Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Frederica
9.6 out of 10, Exceptional, (25 reviews)
"We enjoy this place!!!"
United States
nahum f.
The price is ￥13,432
￥32,684 total
includes taxes & fees
Nov 3 - Nov 4
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A living room with two grey sofas, a coffee table, and a ceiling fan.

5. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
The price is ￥15,012
￥50,995 total
includes taxes & fees
Oct 21 - Oct 22
Cambridge Apt in Walkable Neighborhood
A bedroom with a bed, a dresser, a mirror, and a door leading to another room.

6. Cozy Unit in Milford, Delaware -Close to DE Turf

Cozy Unit in Milford, Delaware -Close to DE Turf
Milford
9.6 out of 10, Exceptional, (4 reviews)
"Perfect place for my son and I that had a lacrosse tourney that was only 8 minutes away at the Delaware turf fields Cat was awesome and replied very fast and was super accommodating!! "
United States
Shaine L.
The price is ￥18,773
￥35,420 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Unit in Milford, Delaware -Close to DE Turf
A patio area with outdoor seating, string lights, and potted plants.

7. Poe Themed Home Close to Beaches and DE Turf

Poe Themed Home Close to Beaches and DE Turf
Milford
8.6 out of 10, Excellent, (17 reviews)
"The owner thought of many amenities that I haven't seen before like breakfast bars and oatmeal packets. Very much appreciated."
United States
Sharon
The price is ￥25,599
￥43,501 total
includes taxes & fees
Oct 20 - Oct 21
Poe Themed Home Close to Beaches and DE Turf
A modern living space with a dining area, sofa, and kitchen.

8. Luxury 2 bedroom Apt. Near DE Turf & Beaches!

Luxury 2 bedroom Apt. Near DE Turf & Beaches!
Milford
10.0 out of 10, Exceptional, (1 review)
"This property was perfect for our family while at a lacrosse tournament. It was close to the field and very comfortable. Having two full bathrooms to get ready for the day was a treat! The property was clean and spacious. Also, the host was also extremely responsive. We will definitely return."
United States
Jill M.
The price is ￥12,341
￥53,246 total
includes taxes & fees
Oct 26 - Oct 27
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

9. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is ￥18,962
￥29,455 total
includes taxes & fees
Oct 26 - Oct 27
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A living room with two grey sofas, a coffee table, and a ceiling fan.

10. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
Cambridge
8.0 out of 10, Very good, (4 reviews)
"great location."
United States
Anonymous traveler
The price is ￥10,429
￥51,985 total
includes taxes & fees
Oct 20 - Oct 21
Cambridge Apt in Walkable Neighborhood
A wooden cabin with a porch, a rocking chair, and a table.

11. Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape

Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
Lincoln
10.0 out of 10, Exceptional, (2 reviews)
"Thank you, we had a very pleasant stay"
United States
andy O.
The price is ￥30,024
￥48,915 total
includes taxes & fees
Oct 25 - Oct 26
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

12. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
The price is ￥26,073
￥59,463 total
includes taxes & fees
Nov 17 - Nov 18
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A deck with outdoor furniture, a potted plant, and a house in the background.

13. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is ￥34,764
￥48,910 total
includes taxes & fees
Oct 26 - Oct 27
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

14. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is ￥24,493
￥40,200 total
includes taxes & fees
Oct 20 - Oct 21
Sailwinds Loft at Cambridge Creek
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

15. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (14 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is ￥22,123
￥55,276 total
includes taxes & fees
Oct 20 - Oct 21
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

16. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is ￥29,012
￥43,294 total
includes taxes & fees
Oct 25 - Oct 26
Secluded Cottage in Middle of Chestertown
A modern kitchen with a central island, stainless steel appliances, and a dining area with a chandelier.

17. Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!

Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
Milford
9.4 out of 10, Exceptional, (13 reviews)
"Awesome property! Great price! Excellent communication!"
United States
Krista L.
The price is ￥28,325
￥47,298 total
includes taxes & fees
Oct 20 - Oct 21
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
A modern kitchen with a large island, bar stools, and pendant lighting.

18. Spacious 5 Bedroom w/Pool, Patio and Theater

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.2 out of 10, Wonderful, (12 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
The price is ￥43,775
￥109,586 total
includes taxes & fees
Oct 20 - Oct 21
Spacious 5 Bedroom w/Pool, Patio and Theater
A wooden interior with a dining area, sofas, and a table.

19. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (15 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveler
The price is ￥42,082
￥88,492 total
includes taxes & fees
Oct 20 - Oct 21
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A bedroom with a bed, a bedside table, a window with curtains, and a view of the sea.

20. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!
Cambridge
The price is ￥47,090
￥62,932 total
includes taxes & fees
Oct 20 - Oct 21
More, than just a place to sleep - welcome home!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Caroline County Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Great location. Very clean."
scott 2-night trip
Posted 2 hours ago
St Michaels Inn

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Vacation Apartments in Caroline County

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