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

Vacation Rentals in Kent County

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Our top choices for Kent County vacation rentals

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (135 reviews)
"Easy to find and good parking. Nice quiet neighborhood. Has refrigerator and microwave. Excellent hot water. Thanks"
United States
Donna G.
The price is ￥15,811
￥24,014 total
includes taxes & fees
Nov 16 - Nov 17
First Floor Studio Apartment in Historic Chestertown
A person sitting on a wooden deck by a calm body of water, surrounded by greenery.

2. 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, (34 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is ￥10,860
￥18,622 total
includes taxes & fees
Nov 18 - Nov 19
Guest Suite for up to 2 in a Victorian on the Chester River
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

3. 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, (36 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥21,388
￥46,629 total
includes taxes & fees
Nov 21 - Nov 22
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A house with a front porch, a pathway leading to the entrance, and a bicycle parked outside.

4. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Great hosts… come to Rock Hall every year and found this cute cottage…will def come here every year. Great place"
United States
Nanci H.
BAYSIDE BUNGALOW
A spacious living area with a dining table, sofa, and a kitchen in the background.

5. 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 ￥35,935
￥53,701 total
includes taxes & fees
Nov 16 - Nov 17
Newly restored apartment in the heart of Chestertown
A wooden staircase leading to a beach with a clear view of the sea.

6. 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 ￥30,904
￥57,940 total
includes taxes & fees
Nov 29 - Nov 30
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
An aerial view of a property with a large house surrounded by lush greenery, a driveway, and a road nearby.

7. 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 ￥25,873
￥30,572 total
includes taxes & fees
Nov 23 - Nov 24
Turtle Cove Room
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

8. 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 ￥31,623
￥37,347 total
includes taxes & fees
Dec 16 - Dec 17
Beachcomber Suite
A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

9. Peaceful Farmhouse Getaway on a Working Farm

Peaceful Farmhouse Getaway on a Working Farm
Kennedyville
The price is ￥33,922
￥37,988 total
includes taxes & fees
Nov 16 - Nov 17
Peaceful Farmhouse Getaway on a Working Farm
A riverside dock with boats, a covered seating area, and a bridge in the background.

10. 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 ￥21,561
￥45,709 total
includes taxes & fees
Nov 16 - Nov 17
Historic Chesapeake City Stay
A wooden deck with wicker lounge chairs and a white sofa, overlooking a body of water.

11. Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (8 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is ￥44,666
￥68,904 total
includes taxes & fees
Nov 17 - Nov 18
Long Beach Cottage, (romantic couple’s getaway)
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

12. 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 ￥19,964
￥22,008 total
includes taxes & fees
Nov 16 - Nov 17
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
An outdoor patio with a brick wall, a grill, and metal chairs.

13. 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 ￥39,145
￥46,838 total
includes taxes & fees
Nov 16 - Nov 17
Family Retreat at Lansdowne Manor
A marina with boats docked, a city skyline in the background, and a calm water surface reflecting the lights.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (52 reviews)
"Great stay"
United States
Michael V.
The price is ￥16,290
￥49,062 total
includes taxes & fees
Nov 23 - Nov 24
Charming Coastal/Country Home w/3 Acres & Sauna!
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

15. 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
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is ￥15,172
￥24,160 total
includes taxes & fees
Nov 29 - Nov 30
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A spacious room with a large sliding glass door leading to a deck, a sofa, a chair, and a small table.

16. 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 ￥30,945
￥71,510 total
includes taxes & fees
Nov 19 - Nov 20
Bay Sunsets for Two • Rooftop Fire Pit
A beach with a wooden pier extending into calm waters, surrounded by greenery and a clear sky.

17. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is ￥30,760
￥74,030 total
includes taxes & fees
Nov 16 - Nov 17
Pool Loft Suite | Bay Access & Beach Passes
A kitchen with white cabinets, a wooden island, and a washing machine.

18. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.2 out of 10, Good, (20 reviews)
"Nice place"
United States
christine
The price is ￥12,649
￥15,439 total
includes taxes & fees
Nov 29 - Nov 30
Charming 2-bedroom house in Aberdeen with WiFi and AC
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

19. 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 ￥16,290
￥49,062 total
includes taxes & fees
Nov 23 - Nov 24
Relax on Kent Island in 4 Bedroom Home w/Waterview
A wooden deck with a glass-top table and metal chairs.

20. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (54 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is ￥11,180
￥16,422 total
includes taxes & fees
Nov 23 - Nov 24
Country Get Away Studio Apartment
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 Kent County Hotel Reviews

Hyatt Regency Baltimore Inner Harbor

Hyatt Regency Baltimore Inner Harbor

10/10 Excellent
"Beautiful hotel Friendly staff Clean rooms Great view"
Sylvia 1-night trip
Posted less than an hour ago
Hyatt Regency Baltimore Inner Harbor

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Vacation Apartments in Kent County

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