A river with a green embankment and a boat.

Holiday Rentals in Caroline County

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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, 18, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is €532
includes taxes & fees
15 Sept - 16 Sept
Turnbridge Manor
Property grounds

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, 125, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is €141
includes taxes & fees
15 Sept - 16 Sept
First Floor Studio Apartment in Historic Chestertown
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, 27, (27 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 €112
includes taxes & fees
15 Sept - 16 Sept
Guest Suite for up to 2 in a Victorian on the Chester River
Interior

4. 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, 10, (10 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is €156
includes taxes & fees
21 Sept - 22 Sept
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Room

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, 25, (25 reviews)
"We enjoy this place!!!"
United States
nahum f.
The price is €169
includes taxes & fees
15 Sept - 16 Sept
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Interior

6. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, 107, (107 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
The price is €259
includes taxes & fees
28 Sept - 29 Sept
Cass-Away Luxury Houseboat
Living area

7. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, 50, (50 reviews)
"Had a great time, great property and great location."
United States
Danny B.
The price is €245
includes taxes & fees
8 Oct - 9 Oct
Cass-N-Reel Luxury Houseboat
Room

8. Cozy Unit in Milford, Delaware -Close to DE Turf

Cozy Unit in Milford, Delaware -Close to DE Turf
Milford
10.0 out of 10, 3, (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 €200
includes taxes & fees
15 Sept - 16 Sept
Cozy Unit in Milford, Delaware -Close to DE Turf
Terrace/patio

9. 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, 1, (1 review)
"Thank you, we had a very pleasant stay"
United States
andy O.
The price is €274
includes taxes & fees
15 Sept - 16 Sept
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
Outdoor dining

10. Poe Themed Home Close to Beaches and DE Turf

Poe Themed Home Close to Beaches and DE Turf
Milford
8.6 out of 10, 16, (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 €239
includes taxes & fees
28 Sept - 29 Sept
Poe Themed Home Close to Beaches and DE Turf
Private kitchen

11. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, 39, (39 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is €224
includes taxes & fees
21 Sept - 22 Sept
Sailwinds Loft at Cambridge Creek
Dining

12. 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, 16, (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 €441
includes taxes & fees
15 Sept - 16 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Pool

13. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, 6, (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 €217
includes taxes & fees
21 Sept - 22 Sept
Mini Aruba RV/Glamping Tent
Room

14. Pet-Friendly Pond Cottage • Nature Escape Near Beaches

Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Seaford
The price is €126
includes taxes & fees
12 Oct - 13 Oct
Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Interior

15. Luxury 2 bedroom Apt. Near DE Turf & Beaches!

Luxury 2 bedroom Apt. Near DE Turf & Beaches!
Milford
10.0 out of 10, 1, (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 €303
includes taxes & fees
21 Sept - 22 Sept
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
Marina

16. 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, 25, (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 €334
includes taxes & fees
30 Sept - 1 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Dining

17. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, 12, (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 €359
includes taxes & fees
30 Sept - 1 Oct
Family Retreat at Lansdowne Manor
Living area

18. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, 2, (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 €240
includes taxes & fees
21 Sept - 22 Sept
Secluded Cottage in Middle of Chestertown
Living area

19. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is €255
includes taxes & fees
5 Oct - 6 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Living area

20. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, 33, (33 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is €302
includes taxes & fees
15 Sept - 16 Sept
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

St Michaels Inn

St Michaels Inn

8/10 Good
"The one issue was there were flies in our room and a squished bug came on our wall. There also were cobwebs in the corner. Not enough pillows and old."
Rachel 1-night trip
Posted 2 hours ago
St Michaels Inn

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Holiday Homes in Caroline County

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