A river with a green embankment and a boat.

Search 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)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is £474
includes taxes & fees
28 Sept - 29 Sept
Turnbridge Manor
A bedroom with a bunk bed, a single bed, a desk, and a chair.

2. 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 £148
includes taxes & fees
30 Sept - 1 Oct
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
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, (28 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 £98
includes taxes & fees
29 Sept - 30 Sept
Guest Suite for up to 2 in a Victorian on the Chester River
A modern exterior with a black door, a metal staircase, and a lantern.

4. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (107 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
The price is £233
includes taxes & fees
28 Sept - 29 Sept
Cass-Away Luxury Houseboat
A modern kitchen with dark cabinets, a white countertop, and a large window.

5. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
The price is £209
includes taxes & fees
8 Oct - 9 Oct
Cass-N-Reel Luxury Houseboat
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

6. 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
9.8 out of 10, Exceptional, (10 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is £145
includes taxes & fees
4 Oct - 5 Oct
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A modern living space with a dining area, sofa, and kitchen.

7. 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 £254
includes taxes & fees
29 Sept - 30 Sept
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

8. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is £123
includes taxes & fees
30 Sept - 1 Oct
First Floor Studio Apartment in Historic Chestertown
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
10.0 out of 10, Exceptional, (3 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 £171
includes taxes & fees
25 Oct - 26 Oct
Cozy Unit in Milford, Delaware -Close to DE Turf
A wooden cabin with a porch, a rocking chair, and a table.

10. 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 £235
includes taxes & fees
26 Oct - 27 Oct
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
A patio area with outdoor seating, string lights, and potted plants.

11. 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, (16 reviews)
"Theme decor was awesome. Location was a quick stroll downtown. Very busy street so use a white noise app on your phone if street noise is an issue."
United States
Dee Z. B.
The price is £210
includes taxes & fees
26 Oct - 27 Oct
Poe Themed Home Close to Beaches and DE Turf
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, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is £302
includes taxes & fees
27 Oct - 28 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A swimming pool with a tiled edge, surrounded by potted plants and outdoor furniture.

13. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My son and I had a great stay here for the weekend, camper was clean and had everything we needed and the family was happy to join us or let us have our privacy. All you could ask for and the backyard pool area is as good as it looks in the pictures. Would go back anytime we are in the area."
United States
Robert N.
The price is £195
includes taxes & fees
26 Oct - 27 Oct
Mini Aruba RV/Glamping Tent
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 £196
includes taxes & fees
28 Sept - 29 Sept
Sailwinds Loft at Cambridge Creek
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

15. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is £385
includes taxes & fees
28 Sept - 29 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

16. 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 £279
includes taxes & fees
28 Sept - 29 Sept
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A kitchen with wooden cabinets, a dining table, and a refrigerator.

17. 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 £264
includes taxes & fees
29 Sept - 30 Sept
Family Retreat at Lansdowne Manor
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 £210
includes taxes & fees
27 Oct - 28 Oct
Secluded Cottage in Middle of Chestertown
A deck with outdoor furniture, a potted plant, and a house in the background.

19. 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 £235
includes taxes & fees
7 Oct - 8 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

20. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Host was great"
United States
mark o.
The price is £404
includes taxes & fees
29 Sept - 30 Sept
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
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

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Staff was perfect and the property is bigger than Rhode Island."
John 1-night trip
Posted 4 hours ago
Hyatt Regency Chesapeake Bay

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, apart-hotels, 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 depends 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 selected for you start as low as £517 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. 

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