A coastal town with a marina, a bridge, and a highway.

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Our top choices for Kent County holiday rentals

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is £114
includes taxes & fees
16 Nov - 17 Nov
First Floor Studio Apartment in Historic Chestertown

2. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (35 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 £251
includes taxes & fees
15 Nov - 16 Nov
Newly restored apartment in the heart of Chestertown

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, (32 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is £89
includes taxes & fees
12 Nov - 13 Nov
Guest Suite for up to 2 in a Victorian on the Chester River

4. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is £225
includes taxes & fees
12 Nov - 13 Nov
BAYSIDE BUNGALOW

5. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (34 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is £213
includes taxes & fees
12 Nov - 13 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

6. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
The price is £144
includes taxes & fees
23 Nov - 24 Nov
Turtle Cove Room

7. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is £154
includes taxes & fees
23 Nov - 24 Nov
Beachcomber Suite

8. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is £264
includes taxes & fees
23 Nov - 24 Nov
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

9. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 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 £215
includes taxes & fees
12 Nov - 13 Nov
Family Retreat at Lansdowne Manor

10. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is £193
includes taxes & fees
12 Nov - 13 Nov
Cass-N-Reel Luxury Houseboat

11. The Marle

The Marle
4.5 star property
Old Goucher
10.0 out of 10, Exceptional, (1 review)
"I I love Baltimore and these great mansions that have been restored are an awesome way to appreciate this town."
United States
Anonymous traveller
The price is £230
includes taxes & fees
12 Nov - 13 Nov
The Marle

12. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is £219
includes taxes & fees
12 Nov - 13 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!

13. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is £110
includes taxes & fees
12 Nov - 13 Nov
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

14. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"Cute place. Clean, comfortable, and convenient to the soccer complex. I wasn’t familiar with Chesapeake City but we had a great time at the waterfront restaurants."
United States
John P.
The price is £224
includes taxes & fees
12 Nov - 13 Nov
Historic Chesapeake City Stay

15. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is £407
includes taxes & fees
15 Nov - 16 Nov
Bohemia Manor Farm

16. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is £224
includes taxes & fees
15 Nov - 16 Nov
Relax on Kent Island in 4 Bedroom Home w/Waterview

17. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Great stay, exactly as advertised, Donna was great!"
United States
Sam C.
The price is £933
includes taxes & fees
1 Dec - 2 Dec
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

18. Bay Sunsets for Two • Rooftop Fire Pit

Bay Sunsets for Two • Rooftop Fire Pit
Pasadena
10.0 out of 10, Exceptional, (4 reviews)
"We had a phenomenal time celebrating our engagement at Flohom! The space was spotlessly clean, super comfortable, and peaceful. The location was fantastic, and the hosting was top-notch from start to finish. We couldn't have asked for a better experience to"
United States
Charles W.
The price is £337
includes taxes & fees
15 Nov - 16 Nov
Bay Sunsets for Two • Rooftop Fire Pit
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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Holiday Apartments in Kent County

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