A river with a green embankment and a boat.

Holiday Rentals in Caroline County

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Our top choices for Caroline County holiday 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 €567
includes taxes & fees
2 Nov - 3 Nov
Turnbridge Manor
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

2. 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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is €116
includes taxes & fees
2 Nov - 3 Nov
Guest Suite for up to 2 in a Victorian on the Chester River
A deck with a view of a marina, including boats and docks.

3. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is €248
includes taxes & fees
12 Nov - 13 Nov
Cass-N-Reel Luxury Houseboat
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (132 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is €146
includes taxes & fees
2 Nov - 3 Nov
First Floor Studio Apartment in Historic Chestertown
A bedroom with a bunk bed, a single bed, a desk, and a chair.

5. 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 €183
includes taxes & fees
30 Nov - 1 Dec
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A living room with two grey sofas, a coffee table, and a ceiling fan.

6. 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 €288
includes taxes & fees
10 Nov - 11 Nov
Cambridge Apt in Walkable Neighborhood
A waterfront patio with outdoor seating and umbrellas, overlooking a river with boats and a bridge in the background.

7. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (110 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
Cass-Away Luxury Houseboat
A living room with two grey sofas, a coffee table, and a ceiling fan.

8. 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 traveller
The price is €299
includes taxes & fees
31 Oct - 1 Nov
Cambridge Apt in Walkable Neighborhood
A bedroom with a bed, a dresser, a mirror, and a door leading to another room.

9. 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 €197
includes taxes & fees
31 Oct - 1 Nov
Cozy Unit in Milford, Delaware -Close to DE Turf
A modern living space with a dining area, sofa, and kitchen.

10. 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 €282
includes taxes & fees
2 Nov - 3 Nov
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.

11. 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.
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
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 €338
includes taxes & fees
17 Nov - 18 Nov
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A garden with a wooden bridge, lush greenery, and a variety of plants.

13. 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 €236
includes taxes & fees
3 Nov - 4 Nov
Secluded Cottage in Middle of Chestertown
A patio area with outdoor seating, string lights, and potted plants.

14. 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 €238
includes taxes & fees
31 Oct - 1 Nov
Poe Themed Home Close to Beaches and DE Turf
Living area

15. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Easton
10.0 out of 10, Exceptional, (1 review)
"Fabulous location in town location! It was much larger than we expected - 2 levels. Nice open layout on the main level with 2 BR/BA and a 3rd BR/BA on 2nd floor. Owners are very responsive before and during the trip. We could not connect to the TV, but owner quickly offered assistance. Bathrooms can use some towel racks and shelves. Beds/pillows were comfy! We were very happy with our stay."
United States
Lynn G.
The price is €379
includes taxes & fees
4 Nov - 5 Nov
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
A single-story house with a garage, a front lawn, and a driveway.

16. A pleasant 3-bedroom house in a peaceful, quiet neighborhood in Milford

A pleasant 3-bedroom house in a peaceful, quiet neighborhood in Milford
Milford
The price is €262
includes taxes & fees
2 Nov - 3 Nov
A pleasant 3-bedroom house in a peaceful, quiet neighborhood in Milford
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

17. 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 €230
includes taxes & fees
5 Nov - 6 Nov
Sailwinds Loft at Cambridge Creek
A wooden cabin with a porch, a rocking chair, and a table.

18. 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 €281
includes taxes & fees
22 Nov - 23 Nov
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.

19. 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, (15 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is €335
includes taxes & fees
1 Nov - 2 Nov
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

20. 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 €258
includes taxes & fees
5 Nov - 6 Nov
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
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

Red Roof Inn & Suites Dover Downtown

Red Roof Inn & Suites Dover Downtown

10/10 Excellent
"."
Daniel J 2-night trip
Posted 10 hours ago
Red Roof Inn & Suites Dover Downtown

Find out more about Caroline County

Holiday Homes in Caroline County

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