A river with a green embankment and a boat.

Vacation Rentals in Caroline County

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Our top choices for Caroline County vacation rentals

Property grounds

1. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (17 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is ￥57,161
￥96,777 total
includes taxes & fees
Sep 8 - Sep 9
Turnbridge Manor
Exterior

2. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store
Hartly
The price is ￥16,354
￥24,236 total
includes taxes & fees
Sep 12 - Sep 13
Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store
Property grounds

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is ￥15,719
￥25,220 total
includes taxes & fees
Sep 10 - Sep 11
First Floor Studio Apartment in Historic Chestertown
Room

4. 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 ￥13,496
￥32,523 total
includes taxes & fees
Oct 4 - Oct 5
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Exterior

5. 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, (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 ￥10,797
￥19,860 total
includes taxes & fees
Sep 14 - Sep 15
Guest Suite for up to 2 in a Victorian on the Chester River
Interior

6. 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 ￥13,570
￥55,281 total
includes taxes & fees
Sep 9 - Sep 10
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
Room

7. 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 ￥18,863
￥35,590 total
includes taxes & fees
Sep 15 - Sep 16
Cozy Unit in Milford, Delaware -Close to DE Turf
Interior

8. 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 ￥17,623
￥28,029 total
includes taxes & fees
Sep 10 - Sep 11
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
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, Exceptional, (1 review)
"Thank you, we had a very pleasant stay"
United States
andy O.
The price is ￥30,168
￥48,991 total
includes taxes & fees
Sep 16 - Sep 17
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
Marina

10. 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 ￥26,435
￥60,797 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Private kitchen

11. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is ￥24,611
￥40,394 total
includes taxes & fees
Sep 10 - Sep 11
Sailwinds Loft at Cambridge Creek
Exterior

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

Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Seaford
The price is ￥19,054
￥23,563 total
includes taxes & fees
Sep 10 - Sep 11
Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Marina

13. 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, (13 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is ￥24,032
￥58,250 total
includes taxes & fees
Sep 8 - Sep 9
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Dining

14. 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 ￥39,695
￥66,481 total
includes taxes & fees
Sep 14 - Sep 15
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
House (3 Bedrooms) | Interior

15. Getaway on 1/2 Acre w/ Deck in Georgetown

Getaway on 1/2 Acre w/ Deck in Georgetown
3.0 star property
Georgetown
10.0 out of 10, Exceptional, (1 review)
"This place is just as you see in the photos; clean, welcoming, great location, and very peaceful. We are certainly looking forward to staying here next year, if available. The contact person was available and answered quickly when I contacted him. "
United States
ANA
The price is ￥23,070
￥52,469 total
includes taxes & fees
Sep 8 - Sep 9
Getaway on 1/2 Acre w/ Deck in Georgetown
Private kitchen

16. 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
9.0 out of 10, Wonderful, (7 reviews)
The price is ￥32,547
￥52,115 total
includes taxes & fees
Sep 8 - Sep 9
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
Interior

17. Cozy Room in Dover

Cozy Room in Dover
Dover
The price is ￥9,289
￥15,264 total
includes taxes & fees
Sep 7 - Sep 8
Cozy Room in Dover
Outdoor dining

18. 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, (15 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 ￥25,954
￥44,425 total
includes taxes & fees
Sep 8 - Sep 9
Poe Themed Home Close to Beaches and DE Turf
Pool

19. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"We had an absolutely wonderful stay at this adorable glamping camper oasis while in town for the NASCAR All-Star Race weekend. The camper and property were spotless, beautifully maintained, and it has so many thoughtful amenities that made our stay comfortable and relaxing.The heated pool was amazing after a long day, and the entire atmosphere was peaceful, welcoming, and fun. The hosts were incredibly friendly, gracious, and accommodating throughout our stay. You can truly tell they take...
United States
Roberta J.
The price is ￥25,634
￥41,527 total
includes taxes & fees
Sep 9 - Sep 10
Mini Aruba RV/Glamping Tent
Living area

20. 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 ￥30,009
￥45,779 total
includes taxes & fees
Sep 9 - Sep 10
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
"We had a great stay . It's a dated hotel but was great for the price . .Staff were nice . The place was clean ,bed Breakfast was really good had a good amount of choices.Price was perfect for the place . Will stay there again in the future ."
Fredrick 1-night trip
Posted 1 hour ago
St Michaels Inn

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Vacation Apartments in Caroline County

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