A river with a green embankment and a boat.

Caroline County Vacation Rentals

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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 CA $514
CA $883 total
includes taxes & fees
Oct 14 - Oct 15
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, (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 CA $97
CA $179 total
includes taxes & fees
Oct 19 - Oct 20
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.

3. 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 CA $129
CA $309 total
includes taxes & fees
Oct 28 - Oct 29
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
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, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is CA $141
CA $227 total
includes taxes & fees
Oct 19 - Oct 20
First Floor Studio Apartment in Historic Chestertown
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 CA $136
CA $461 total
includes taxes & fees
Oct 17 - Oct 18
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 CA $169
CA $322 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $231
CA $395 total
includes taxes & fees
Oct 14 - Oct 15
Poe Themed Home Close to Beaches and DE Turf
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

8. 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 CA $135
CA $227 total
includes taxes & fees
Oct 21 - Oct 22
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A modern living space with a dining area, sofa, and kitchen.

9. 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 CA $102
CA $465 total
includes taxes & fees
Oct 15 - Oct 16
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
A kitchen with wooden cabinets, a dining table, and a refrigerator.

10. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 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.
The price is CA $328
CA $410 total
includes taxes & fees
Oct 14 - Oct 15
Family Retreat at Lansdowne Manor
A living room with two grey sofas, a coffee table, and a ceiling fan.

11. 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 CA $94
CA $473 total
includes taxes & fees
Oct 17 - Oct 18
Cambridge Apt in Walkable Neighborhood
A wooden cabin with a porch, a rocking chair, and a table.

12. 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 CA $271
CA $443 total
includes taxes & fees
Oct 25 - Oct 26
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

13. 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 CA $221
CA $363 total
includes taxes & fees
Oct 18 - Oct 19
Sailwinds Loft at Cambridge Creek
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

14. 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 CA $314
CA $442 total
includes taxes & fees
Oct 20 - Oct 21
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A modern kitchen with a large island, bar stools, and pendant lighting.

15. 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 CA $379
CA $983 total
includes taxes & fees
Oct 14 - Oct 15
Spacious 5 Bedroom w/Pool, Patio and Theater
A modern kitchen with a central island, stainless steel appliances, and a dining area with a chandelier.

16. 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, (12 reviews)
"Awesome property! Great price! Excellent communication!"
United States
Krista L.
The price is CA $288
CA $463 total
includes taxes & fees
Oct 14 - Oct 15
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

17. 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)
The price is CA $243
CA $554 total
includes taxes & fees
Nov 3 - Nov 4
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

18. 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 CA $262
CA $393 total
includes taxes & fees
Oct 14 - Oct 15
Secluded Cottage in Middle of Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

19. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is CA $321
CA $500 total
includes taxes & fees
Oct 18 - Oct 19
Newly restored apartment in the heart of Chestertown
A covered patio with a table and chairs, a white fence, and a view of the greenery.

20. Getaway on 1/2 Acre w/ Deck in Georgetown

Getaway on 1/2 Acre w/ Deck in Georgetown
3.0 star property
Georgetown
10.0 out of 10, Exceptional, (1 review)
"This place is just as you see in the photos; clean, welcoming, great location, and very peaceful. We are certainly looking forward to staying here next year, if available. The contact person was available and answered quickly when I contacted him. "
United States
ANA
The price is CA $214
CA $476 total
includes taxes & fees
Nov 9 - Nov 10
Getaway on 1/2 Acre w/ Deck in Georgetown
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 Tidewater Inn

The Tidewater Inn

10/10 Excellent
"Very Cs"
Elizabeth 1-night trip
Posted less than an hour ago
The Tidewater Inn

Find out more about Caroline County

Everything you need to know about Caroline County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Caroline County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Caroline County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Caroline County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Caroline County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. 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.  The selection of Caroline County vacation rentals we have selected for you start as low as CA $892 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Caroline County rentals

At Expedia, we put the best Caroline County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Caroline County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Caroline County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Caroline County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.