A river with a green embankment and a boat.

Caroline County Holiday Rentals

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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 AU$877
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 AU$180
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 AU$381
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 AU$228
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 AU$277
includes taxes & fees
17 Nov - 18 Nov
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 AU$458
includes taxes & fees
30 Oct - 31 Oct
Cambridge Apt in Walkable Neighborhood
A marina with floating homes, docks, and boats.

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 AU$455
includes taxes & fees
4 Nov - 5 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 AU$323
includes taxes & fees
30 Oct - 31 Oct
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 AU$431
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.
The price is AU$229
includes taxes & fees
5 Nov - 6 Nov
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A brick building with a white porch and a well-maintained lawn.

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 AU$537
includes taxes & fees
17 Nov - 18 Nov
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A garden path leading to a wooden building with a rustic appearance.

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 AU$406
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 AU$387
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 AU$589
includes taxes & fees
2 Nov - 3 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 AU$420
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 AU$354
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 AU$429
includes taxes & fees
22 Nov - 23 Nov
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
A living room with a dark gray sofa, a small round table, and a green throw blanket. There is a brick accent wall and a ceiling fan.

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 AU$541
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 AU$406
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Our stay was much better than I was expecting! The area was very quiet and the staff friendly and helpful. Continental breakfast was your standard fare and everything clean."
Bobbi 2-night trip
Posted 10 hours ago
St Michaels Inn

Find out more about Caroline County

Everything you need to know about Caroline County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Caroline County holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Caroline County holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Caroline County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Caroline County holiday rentals we have chosen for you start as low as 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 holiday 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 holiday.

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.