A river with a green embankment and a boat.

Caroline County Holiday Rentals

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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, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is HK$2,822
HK$4,778 total
includes taxes & fees
16 Sept - 17 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, Exceptional, (125 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is HK$776
HK$1,245 total
includes taxes & fees
9 Sept - 10 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, 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 HK$533
HK$981 total
includes taxes & fees
10 Sept - 11 Sept
Guest Suite for up to 2 in a Victorian on the Chester River
Interior

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 HK$784
HK$2,458 total
includes taxes & fees
25 Sept - 26 Sept
Cass-Away Luxury Houseboat
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)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is HK$862
HK$1,372 total
includes taxes & fees
14 Sept - 15 Sept
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
1 bedroom, desk, iron/ironing board, WiFi

6. 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 HK$627
HK$1,557 total
includes taxes & fees
4 Oct - 5 Oct
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Terrace/patio

7. 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 HK$1,490
HK$2,419 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
1 bedroom, iron/ironing board, WiFi, bed sheets

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, 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 HK$931
HK$1,757 total
includes taxes & fees
9 Sept - 10 Sept
Cozy Unit in Milford, Delaware -Close to DE Turf
Private kitchen

9. 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 HK$1,215
HK$1,994 total
includes taxes & fees
22 Sept - 23 Sept
Sailwinds Loft at Cambridge Creek
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 HK$1,372
HK$3,050 total
includes taxes & fees
30 Sept - 1 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Dining

11. 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 HK$1,960
HK$3,282 total
includes taxes & fees
16 Sept - 17 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Interior

12. 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
Getaway on 1/2 Acre w/ Deck in Georgetown
Pool

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 HK$1,254
HK$2,001 total
includes taxes & fees
16 Sept - 17 Sept
Mini Aruba RV/Glamping Tent
Interior

14. 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 HK$630
HK$2,676 total
includes taxes & fees
9 Sept - 10 Sept
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
Marina

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, (13 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is HK$1,294
HK$2,950 total
includes taxes & fees
9 Sept - 10 Sept
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Outdoor dining

16. 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)
"Good for what we needed. House was a little too themey but served the purpose for us."
United States
Vincent F.
The price is HK$1,270
HK$2,150 total
includes taxes & fees
13 Sept - 14 Sept
Poe Themed Home Close to Beaches and DE Turf
1 bedroom, free WiFi

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

Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Seaford
The price is HK$941
HK$1,163 total
includes taxes & fees
16 Sept - 17 Sept
Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Dining

18. 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 HK$2,603
HK$3,247 total
includes taxes & fees
23 Sept - 24 Sept
Family Retreat at Lansdowne Manor
TV, fireplace

19. 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 HK$1,439
HK$2,206 total
includes taxes & fees
22 Sept - 23 Sept
Secluded Cottage in Middle 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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Not our first time and won’t be the last. We love the staff, food is great at breakfast and the lite fare bar/lobby menu, rooms are large and comfortable and overall great place to stay."
Michael 2-night trip
Posted 2 hours ago
Hyatt Place Kent Narrows & Marina