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

Vacation Rentals in Kent County

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Top Cities in Kent County

A coastal landscape with a sandy beach, a rocky barrier, and a calm sea.
Vacation RentalsVacation Rentals

Rock Hall

Rock Hall
An aerial view of a town with a river, buildings, and surrounding greenery.
Vacation RentalsVacation Rentals

Chestertown

Chestertown

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
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Oct 19 - Oct 20
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

2. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 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.
$319 nightly
The price is $352
Oct 18 - Oct 19
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

3. 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.
$264 nightly
The price is $274
Oct 18 - Oct 19
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
A hallway with wooden flooring, a door on the right, and a window at the end.

4. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
$473 nightly
The price is $493
Oct 28 - Oct 29
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$259 nightly
The price is $286
Oct 17 - Oct 18
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

6. 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, (29 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.
$118 nightly
The price is $125
Oct 19 - Oct 20
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
A building with a gabled roof and a circular vent on the roof.

7. 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.
$286 nightly
The price is $316
Oct 20 - Oct 21
Total with taxes and fees
BAYSIDE BUNGALOW
A house with a covered porch, a grill, and a propane tank in the yard.

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

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
$314 nightly
The price is $347
Oct 20 - Oct 21
Total with taxes and fees
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

9. 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.
$197 nightly
The price is $214
Oct 19 - Oct 20
Total with taxes and fees
Beachcomber Suite
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

10. Turtle Cove Room

Turtle Cove Room
Kent County
$183 nightly
The price is $199
Oct 19 - Oct 20
Total with taxes and fees
Turtle Cove Room
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

11. 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, (11 reviews)
"The host was incredibly friendly and communicative. The place was a lot bigger than I expected, and it was beautiful to sit out by the fire pit and look at the river nearby. And, she left us snacks and smores for the stay! A nice quiet spot to spend a night."
United States
Matthew
$145 nightly
The price is $154
Nov 2 - Nov 3
Total with taxes and fees
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A dining table with a wine bottle, glasses, and a red bowl with a leaf pattern.

12. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
$402 nightly
The price is $451
Nov 5 - Nov 6
Total with taxes and fees
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A hotel room with two beds, a fireplace, a large window, and a modern chandelier.

13. The Marle

The Marle
4.5 star property
Old Goucher
$282 nightly
The price is $331
Oct 28 - Oct 29
Total with taxes and fees
The Marle
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
$259 nightly
The price is $278
Oct 18 - Oct 19
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
A riverside dock with boats, a covered seating area, and a bridge in the background.

15. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (30 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
$263 nightly
The price is $279
Oct 19 - Oct 20
Total with taxes and fees
Historic Chesapeake City Stay
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

16. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
10.0 out of 10, Exceptional, (2 reviews)
$408 nightly
The price is $465
Oct 27 - Oct 28
Total with taxes and fees
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

17. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
$271 nightly
The price is $292
Oct 19 - Oct 20
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

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

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
$89 nightly
The price is $95
Oct 27 - Oct 28
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
Room

19. Wyatt's Saloon Guest House 2

Wyatt's Saloon Guest House 2
2.0 star property
Fells Point
$421 nightly
The price is $495
Nov 12 - Nov 13
Total with taxes and fees
Wyatt's Saloon Guest House 2
Three birds perched on a wooden structure by the water.

20. 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)
"Just what was needed for our weekend stay."
United States
barbara s.
$1,200 nightly
The price is $1,325
Oct 18 - Oct 19
Total with taxes and fees
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kent County Hotel Reviews

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

10/10 Excellent
"Arrived in Baltimore early checked into my room, but did not receive a room until 11pm"
Reggie 2-night trip
Posted 1 hour ago
Renaissance Baltimore Harborplace Hotel

Find out more about Kent County

Discover your perfect Kent County vacation rental with Expedia

How many vacation rentals are available in Kent County?


Expedia has plenty of vacation rentals to choose from in and around  Kent County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Kent County?


The selection of Kent County vacation rentals we have selected for you start as low as $209 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Kent County?


Vacation rentals in Kent County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Kent County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Kent County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Kent County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Kent County?


Find vacation rentals in Kent County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Kent County.  


What amenities are available in a vacation rental in Kent County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Kent County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Kent County?   


Everytime is a great time to head to Kent County! Staying in a Kent County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Kent County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Kent County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Kent County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Kent County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.