A river with a green embankment and a boat.

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Our top choices for Caroline County holiday rentals

Property grounds

1. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (15 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is £449
includes taxes & fees
12 Aug - 13 Aug
Turnbridge Manor
1 bedroom, desk, iron/ironing board, WiFi

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 £140
includes taxes & fees
16 Aug - 17 Aug
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Exterior

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, (26 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 £96
includes taxes & fees
10 Sept - 11 Sept
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (119 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is £121
includes taxes & fees
12 Aug - 13 Aug
First Floor Studio Apartment in Historic Chestertown
Interior

5. 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)
"The pictures were accurate. Our host communicated with us in a timely manner. Everything was as it said it was going to be everything in the house worked and made sense. We really enjoyed our stay. We definitely will be staying at this location again when we come in into Dover."
United States
Laura
The price is £124
includes taxes & fees
9 Sept - 10 Sept
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
1 bedroom, iron/ironing board, WiFi, bed sheets

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)
"The unit is tiny but knowing we wouldn’t be spending much time there, it was fine for our use. I liked that we could walk to locations in town. Her directions for use were very clear and precise."
United States
Rebecca N.
The price is £174
includes taxes & fees
9 Sept - 10 Sept
Cozy Unit in Milford, Delaware -Close to DE Turf
Interior

7. Cozy Room in Dover

Cozy Room in Dover
Dover
The price is £74
includes taxes & fees
16 Aug - 17 Aug
Cozy Room in Dover
Interior

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.
The price is £293
includes taxes & fees
9 Sept - 10 Sept
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
Outdoor dining

9. Poe Themed Home Close to Beaches and DE Turf

Poe Themed Home Close to Beaches and DE Turf
Milford
9.0 out of 10, Wonderful, (14 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 £203
includes taxes & fees
12 Aug - 13 Aug
Poe Themed Home Close to Beaches and DE Turf
Terrace/patio

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, (1 review)
"Thank you, we had a very pleasant stay"
United States
andy O.
The price is £218
includes taxes & fees
25 Aug - 26 Aug
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
Private kitchen

11. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (38 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is £185
includes taxes & fees
13 Aug - 14 Aug
Sailwinds Loft at Cambridge Creek
1 bedroom, iron/ironing board, WiFi, bed sheets

12. Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
The price is £204
includes taxes & fees
25 Aug - 26 Aug
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Interior

13. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 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 £297
includes taxes & fees
2 Sept - 3 Sept
Family Retreat at Lansdowne Manor
Pool

14. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
United States
Marleen M.
The price is £174
includes taxes & fees
9 Sept - 10 Sept
Mini Aruba RV/Glamping Tent
Dining

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, (15 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 £309
includes taxes & fees
12 Aug - 13 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Marina

16. Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very good, (9 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is £290
includes taxes & fees
31 Aug - 1 Sept
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
TV, fireplace

17. 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 £211
includes taxes & fees
19 Aug - 20 Aug
Secluded Cottage in Middle of Chestertown
Marina

18. 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, (24 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 £388
includes taxes & fees
8 Sept - 9 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Coffee/tea maker, fridge, microwave, oven

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
8.8 out of 10, Excellent, (6 reviews)
The price is £226
includes taxes & fees
23 Aug - 24 Aug
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
Smart TV, books

20. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is £261
includes taxes & fees
20 Aug - 21 Aug
Newly restored apartment in the heart of Chestertown
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

8/10 Good
"I enjoyed my stay. Beautiful site, clean rooms, friendly staff. It's older but well maintained. I will definitely recommend and stay again for a relaxing low stress getaway"
Tamika 2-night trip
Posted less than an hour ago
Bally's Dover Casino Resort

Find out more about Caroline County

Holiday Apartments in Caroline County

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