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

Kent County holiday homes

We found 305 holiday rentals — enter your dates for availability

Discover a selection of 74 homes, 14 apartments and other holiday rentals in Kent County that are perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as a fireplace and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Popular Kent County destinations on Bookabach

A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Chestertown

Two people in a red canoe on a body of water with a sunset and a bridge in the background.

Rock Hall

Holiday rentals with weekly discounts – Kent County

Showing deals for:18 Dec - 25 Dec

Exceptional

(31 reviews)

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville

12% off

NZ$3,675

for 7 nights, 1 room

NZ$525 per night

includes taxes & fees

SuperMoon rising behind the house with moon beams on the bay

Exceptional

(47 reviews)

Sunset Lodge on the Bay

Rock Hall

9% off

NZ$14,073

for 7 nights, 1 home

NZ$2,010 per night

includes taxes & fees

Exceptional

(107 reviews)

Cass-Away Luxury Houseboat

Grasonville

7% off

NZ$2,277

for 7 nights, 1 houseboat

NZ$325 per night

includes taxes & fees

Beautiful waterfront home on Burley Creek with private pier

Enjoy screened in porch with dining table and sitting area

Lawn for yard games along the waterfront, or simply relax in the shade

Exceptional

(62 reviews)

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Annapolis

8% off

NZ$9,074

for 7 nights, 1 home

NZ$1,296 per night

includes taxes & fees

3rd floor suite; queen and 2 twins; en-suite bath, sitting area, deck access.

Exceptional

(5 reviews)

Grand home located right on Main St, walk to Chesapeake Bay & great restaurants

Rock Hall

8% off

NZ$9,990

for 7 nights, 1 home

NZ$1,427 per night

includes taxes & fees

New playground, with splash pad, at the park within walking distance.

View from the porch. Enjoy ospreys and eagles, sailboats and ships.

Picnic pavilion by the beach. There is also a grassy area with charcoal grills.

Exceptional

(58 reviews)

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Betterton

11% off

NZ$4,752

for 7 nights, 1 home

NZ$679 per night

includes taxes & fees

upstairs bedroom w/ King size bed and space for queen air mattress

Exceptional

(94 reviews)

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena

8% off

NZ$6,714

for 7 nights, 1 home

NZ$959 per night

includes taxes & fees

Local artwork is displayed and for sale, if you wish to take a memory home.

Quiet, tree-filled neighborhood. The apartment is above the garage.

Exceptional

(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

8% off

NZ$3,027

for 7 nights, 1 apartment

NZ$432 per night

includes taxes & fees

Exceptional

(39 reviews)

This is truly a Baydream!

Rock Hall

8% off

NZ$3,631

for 7 nights, 1 home

NZ$519 per night

includes taxes & fees

Exceptional

(66 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off

NZ$6,497

for 7 nights, 1 home

NZ$928 per night

includes taxes & fees

Exceptional

(24 reviews)

In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!

Rock Hall

8% off

NZ$3,065

for 7 nights, 1 home

NZ$438 per night

includes taxes & fees

Exceptional

(63 reviews)

Beautiful Retreat Located in Rock Hall - walk to everything!

Rock Hall

13% off

NZ$4,008

for 7 nights, 1 home

NZ$573 per night

includes taxes & fees

Screen porch for relaxing, eating, watching the water, working on a laptop

Exceptional

(59 reviews)

Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!

Annapolis

15% off

NZ$6,051

for 7 nights, 1 home

NZ$864 per night

includes taxes & fees

Exceptional

(68 reviews)

Brand New Cottage Steps from the Beach!

Rock Hall

8% off

NZ$3,321

for 7 nights, 1 home

NZ$474 per night

includes taxes & fees

Exceptional

(9 reviews)

Brand New Modern Rock Hall home with Water Views

Rock Hall

8% off

NZ$4,422

for 7 nights, 1 home

NZ$632 per night

includes taxes & fees

Exceptional

(217 reviews)

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville

12% off

NZ$5,820

for 7 nights, 1 room

NZ$831 per night

includes taxes & fees

Exceptional

(11 reviews)

Cute waterfront apartment -- 8 min from the beach!

Rock Hall

8% off

NZ$2,906

for 7 nights, 1 apartment

NZ$415 per night

includes taxes & fees

Exceptional

(14 reviews)

Knot's Landing, spacious Apt. downtown Rock Hall

Rock Hall

8% off

NZ$2,887

for 7 nights, 1 apartment

NZ$412 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - Kent County

STONE RIVERSIDE COTTAGE is just a few steps from the SASSAFRAS RIVERS edge

Sleeps 4 · 1 bedroom · 1 bathroom

Premier Host

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Sleeps 28 · 9 bedrooms · 5+ bathrooms

Premier Host

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Sleeps 14 · 6 bedrooms · 3+ bathrooms

Premier Host

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Life is better at the RIVER!--Cozy waterfront cottage

Sleeps 5 · 3 bedrooms · 2 bathrooms

Sunset Lodge on the Bay

Sleeps 14 · 6 bedrooms · 4 bathrooms

Book a holiday rental for your Kent County getaway

Learn about the unique charm of Kent County with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Kent County

Are you searching for attractions to see while you're in town? Venture out of your cosy holiday rental and experience everything that makes Kent County a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

Queenstown Harbor Golf (16.1 mi / 25.9 km)
Bulle Rock Golf Course (23.3 mi / 37.5 km)
Bay Hills Golf Club (24.8 mi / 39.9 km)
Dover International Speedway (28.7 mi / 46.3 km)
Crow Farm and Vineyard (10.6 mi / 17 km)
Paul Reed Smith Guitars (20.3 mi / 32.6 km)

Exploring the natural landscape of Kent County

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Kent County is a great spot to appreciate mother nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

Betterton Beach (11.2 mi / 18 km)
Eastern Neck National Wildlife Refuge (14.9 mi / 24 km)
Miami Beach (17.6 mi / 28.3 km)
Rocky Point Park and Beach (18.3 mi / 29.5 km)
North East Beach Area (20.1 mi / 32.3 km)
Sandy Point Beach (22.3 mi / 35.8 km)

Frequently asked questions

What is the best area to stay in Kent County when booking a holiday home?

Among the more popular neighbourhoods to get a Kent County holiday home is Fairlee. When you lock in your holiday home with Bookabach, you can look forward to having the entire place to yourself. So you won't have to share it with anybody other than your people.

What is the most popular type of holiday home accommodation in Kent County?

According to our research, houses are considered the most popular property type in Kent County. But as you might expect, everyone's idea of an epic stay is bound to be different. Bookabach has holiday homes with every size, shape and budget in mind, so you're bound to find the perfect match.

How much does it cost to rent a holiday home in Kent County?

The average price for a holiday home in Kent County is based on several factors, such as property type, length of stay and time of year. Whether you'd like a villa with space for extended family or an apartment for just you and the kids, just enter your dates of travel to see stays with unbeatable value.

How much does it cost to rent a beach house in Kent County?

The average price for a holiday home by the beach in Kent County depends on when you're travelling and the size and type of property you're searching for. You can find prices quickly and easily on Bookabach by entering your destination and travel dates. Then use the handy filter tool to select the number of bedrooms and amenities that you need, like air conditioning, WiFi and a hot tub.

What are popular home amenities in Kent County?

When it comes to home amenities that guests prefer in Kent County, off-street parking options, a microwave oven and a fridge rank the highest. With Bookabach holiday homes, you'll discover options to fit your style and taste, whether you're going on a holiday with family, friends or even pets.

Are there large group holiday homes in Kent County?

With 19 properties that can host 10 guests or more in Kent County, you don't have to keep your invite list short. From family get-togethers to special events like weddings and birthday parties, Bookabach will help you find a large group home to match the occasion.

What are the top attractions for families in Kent County?

You'll find loads of fun things to do and see with the family in Kent County, such as:

Rock Hall Harbour
Historical Society of Kent County Maryland
Eastern Neck National Wildlife Refuge

Can I find two-bedroom holiday homes in Kent County?

Kent County has 20 two-bedroom properties for you to pick from. Enjoy a holiday home with all the space and comfort you need at a price that's hard to resist on Bookabach.

Are there holiday homes with WiFi in Kent County?

You can pick from 43 holiday homes with WiFi in Kent County. If you want to disconnect from daily life on your trip, but still need to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Bookabach.

How old do you have to be to rent a holiday home in Kent County?

The minimum age allowed can differ between properties on Bookabach, so check the rules of the holiday home in Kent County you're interested in. But in general, it's 16, 18 or 21.

How long can I rent a holiday home in Kent County for?

The length of time you can rent a holiday home in Kent County varies according to the property. Just enter your chosen travel dates to look at a list of options offering extended stays. With many amenities such as laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get a terrific place to call your home away from home in Kent County.

More holiday ideas

Holiday Rentals