A river with a green embankment and a boat.

Vacation Rentals in Caroline County

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Top Cities in Caroline County

A calm lake surrounded by tall trees and dense reeds.
Vacation RentalsVacation Rentals

Denton

Denton
A forest with tall trees and a sunset in the background.
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Ridgely

Ridgely

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.
$528 nightly
The price is $560
Nov 3 - Nov 4
Total with taxes and fees
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
$110 nightly
The price is $117
Nov 3 - Nov 4
Total with taxes and fees
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
$232 nightly
The price is $257
Nov 12 - Nov 13
Total with taxes and fees
Cass-N-Reel Luxury Houseboat
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.
$236 nightly
The price is $241
Nov 3 - Nov 4
Total with taxes and fees
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
$291 nightly
The price is $323
Nov 3 - Nov 4
Total with taxes and fees
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.
$209 nightly
The price is $214
Nov 3 - Nov 4
Total with taxes and fees
Cozy Unit in Milford, Delaware -Close to DE Turf
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

7. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$136 nightly
The price is $150
Nov 3 - Nov 4
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
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.
$284 nightly
The price is $303
Nov 5 - Nov 6
Total with taxes and fees
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.
$138 nightly
The price is $141
Nov 3 - Nov 4
Total with taxes and fees
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
$285 nightly
The price is $315
Nov 3 - Nov 4
Total with taxes and fees
Cambridge Apt in Walkable Neighborhood
Living area

11. 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.
$378 nightly
The price is $401
Nov 9 - Nov 10
Total with taxes and fees
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
A patio area with outdoor seating, string lights, and potted plants.

12. 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
$256 nightly
The price is $263
Nov 3 - Nov 4
Total with taxes and fees
Poe Themed Home Close to Beaches and DE Turf
A kitchen with wooden cabinets, a dining table, and a refrigerator.

13. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
Family Retreat at Lansdowne Manor
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

14. 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.
$348 nightly
The price is $369
Nov 17 - Nov 18
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A living room with a wooden floor, a desk with a chair, a television, and a shelf with decorative items.

15. Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!

Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!
Seaford
10.0 out of 10, Exceptional, (1 review)
"This was a clean, comfortable place to stay. We only stayed one night, but would've enjoyed staying longer. Sitting outside with coffee in the morning was special. The number of different birds we heard was amazing. We didn't have time to explore the pond, but it added to a nice, quiet stay."
United States
Whitney H.
$136 nightly
The price is $150
Nov 3 - Nov 4
Total with taxes and fees
Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!
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
$283 nightly
The price is $290
Nov 4 - Nov 5
Total with taxes and fees
A pleasant 3-bedroom house in a peaceful, quiet neighborhood in Milford
A wooden cabin with a porch, a rocking chair, and a table.

17. 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.
$287 nightly
The price is $296
Nov 22 - Nov 23
Total with taxes and fees
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

18. 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.
$257 nightly
The price is $272
Nov 8 - Nov 9
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A garden with a wooden bridge, lush greenery, and a variety of plants.

19. 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.
$265 nightly
The price is $275
Nov 4 - Nov 5
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
A modern kitchen with a large island, bar stools, and pendant lighting.

20. 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.
$643 nightly
The price is $655
Nov 3 - Nov 4
Total with taxes and fees
Spacious 5 Bedroom w/Pool, Patio and Theater
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

The Reserve Inn

The Reserve Inn

10/10 Excellent
"The entire place was clean. Staff was friendly 😊"
Tammy 2-night trip
Posted 9 hours ago
The Reserve Inn

Find out more about Caroline County

Discover your perfect Caroline County vacation rental with Expedia

How many vacation rentals are available in Caroline County?


Expedia has plenty of vacation rentals to choose from in and around  Caroline County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Caroline County?


The selection of Caroline County vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Caroline County?


Vacation rentals in Caroline County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Caroline County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Caroline County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Caroline County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Caroline County?


Find vacation rentals in Caroline County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Caroline County.  


What amenities are available in a vacation rental in Caroline County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Caroline County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Caroline County?   


Everytime is a great time to head to Caroline County! Staying in a Caroline County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Caroline County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Caroline County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Caroline County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Caroline County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.