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)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is CA $512
CA $879 total
includes taxes & fees
Oct 13 - Oct 14
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 price is CA $97
CA $178 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 $121
CA $293 total
includes taxes & fees
Nov 9 - Nov 10
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)
"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"
United States
Charr
The price is CA $141
CA $226 total
includes taxes & fees
Oct 12 - Oct 13
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 $135
CA $459 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
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 CA $169
CA $319 total
includes taxes & fees
Oct 14 - Oct 15
Cozy Unit in Milford, Delaware -Close to DE Turf
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

7. 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 $171
CA $267 total
includes taxes & fees
Oct 20 - Oct 21
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A patio area with outdoor seating, string lights, and potted plants.

8. 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)
The price is CA $230
CA $394 total
includes taxes & fees
Oct 12 - Oct 13
Poe Themed Home Close to Beaches and DE Turf
A kitchen with wooden cabinets, a dining table, and a refrigerator.

9. 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 $327
CA $411 total
includes taxes & fees
Oct 12 - Oct 13
Family Retreat at Lansdowne Manor
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 CA $105
CA $473 total
includes taxes & fees
Oct 15 - Oct 16
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
A wooden cabin with a porch, a rocking chair, and a table.

11. 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 $270
CA $442 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
A swimming pool with a tiled edge, surrounded by potted plants and outdoor furniture.

12. 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 CA $213
CA $350 total
includes taxes & fees
Nov 9 - Nov 10
Mini Aruba RV/Glamping Tent
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 $220
CA $360 total
includes taxes & fees
Oct 11 - Oct 12
Sailwinds Loft at Cambridge Creek
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

14. 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 $261
CA $393 total
includes taxes & fees
Oct 13 - Oct 14
Secluded Cottage in Middle of Chestertown
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

15. 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 $249
CA $555 total
includes taxes & fees
Nov 3 - Nov 4
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A living room with two grey sofas, a coffee table, and a ceiling fan.

16. 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 $471 total
includes taxes & fees
Oct 17 - Oct 18
Cambridge Apt in Walkable Neighborhood
A deck with outdoor furniture, a potted plant, and a house in the background.

17. 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 $313
CA $443 total
includes taxes & fees
Oct 19 - Oct 20
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A spacious living area with a dining table, sofa, and a kitchen in the background.

18. 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 $320
CA $502 total
includes taxes & fees
Oct 12 - Oct 13
Newly restored apartment in the heart of Chestertown
A modern kitchen with a central island, stainless steel appliances, and a dining area with a chandelier.

19. 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, (11 reviews)
"Awesome property! Great price! Excellent communication!"
United States
Krista L.
The price is CA $287
CA $455 total
includes taxes & fees
Oct 14 - Oct 15
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
A round window with a view of a garden, a tree, and a building in the background.

20. Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
Kitts Hummock
10.0 out of 10, Exceptional, (1 review)
"Our time here was an attraction in itself. There were so many small details. I won't mention all of them as I don't want to spoil the surprise but one of our favorites was a telescope pointed towards an ocean piling where birds frequently perch. The house felt interactive and playful. There were snacks and beverage options (including tea, coffee, water, and even other surprises) available. Very clean. One consideration is the stairscase. I would advise caution for those with mobility issues (bad...
United States
Alex L.
The price is CA $306
CA $540 total
includes taxes & fees
Oct 18 - Oct 19
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
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

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"Really nice room with great virws of the race track"
Robert 1-night trip
Posted 15 hours ago
Bally's Dover Casino Resort

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 $952 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.