Kent County holiday rentals

We found 304 holiday rentals — enter your dates for availability
Discover a selection of 75 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 Stayz

Holiday rentals with weekly discounts – Kent County

Showing deals for:25 Dec - 1 Jan

Kitchen
Kitchen
Kitchen
Exterior
Exceptional
(31 reviews)

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

Stevensville

12% off
AU$3,131
for 7 nights, 1 room
AU$447 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
SuperMoon rising behind the house with moon beams on the bay
Interior
Dining
Interior
Exceptional
(47 reviews)

Sunset Lodge on the Bay

Rock Hall

9% off
AU$11,340
for 7 nights, 1 home
AU$1,620 per night
includes taxes & fees
Sunset Lodge on the Bay
Interior
Interior
Private kitchen
Room
Exceptional
(107 reviews)

Cass-Away Luxury Houseboat

Grasonville

7% off
AU$2,092
for 7 nights, 1 houseboat
AU$299 per night
includes taxes & fees
Cass-Away Luxury Houseboat
Exterior detail
Terrace/patio
Room
Private kitchen
Exceptional
(5 reviews)

Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.

Stevensville

17% off
AU$6,850
for 7 nights, 1 home
AU$979 per night
includes taxes & fees
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.
Sitting area overlooking Burley Creek
Enjoy screened in porch with dining table and sitting area
Beautiful waterfront home on Burley Creek with private pier
West-facing screened porch with bar area and café lights for night ambience
Exceptional
(63 reviews)

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

Annapolis

8% off
AU$8,137
for 7 nights, 1 home
AU$1,162 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
3rd floor suite; queen and 2 twins; en-suite bath, sitting area, deck access.
Exterior
Dining
Interior
Exceptional
(5 reviews)

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

Rock Hall

8% off
AU$7,899
for 7 nights, 1 home
AU$1,128 per night
includes taxes & fees
Grand home located right on Main St, walk to Chesapeake Bay & great restaurants
Expansive front porch overlooking the Chesapeake Bay and Sassafras River!
View from the porch. Enjoy ospreys and eagles, sailboats and ships.
Bedroom 1, with desk and window seat.
New playground, with splash pad, at the park within walking distance.
Exceptional
(58 reviews)

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

Betterton

12% off
AU$3,731
for 7 nights, 1 home
AU$533 per night
includes taxes & fees
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
outdoor space
Terrace/patio
Living room with wood fireplace and second TV with basic channels
Marina
Exceptional
(94 reviews)

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

Pasadena

8% off
AU$5,347
for 7 nights, 1 home
AU$764 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Dining room
New Kitchen 2022
Property grounds
Exterior
Exceptional
(66 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
AU$5,173
for 7 nights, 1 home
AU$739 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Property grounds
Outdoor dining
dining area
kitchen
Exceptional
(39 reviews)

This is truly a Baydream!

Rock Hall

8% off
AU$2,932
for 7 nights, 1 home
AU$419 per night
includes taxes & fees
This is truly a Baydream!
Room
Quiet, tree-filled neighborhood. The apartment is above the garage.
Twin size sofa/futon for a 3rd person.
Local artwork is displayed and for sale, if you wish to take a memory home.
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

7% off
AU$2,466
for 7 nights, 1 apartment
AU$352 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Interior
Front gardens
House front
Private kitchen
Exceptional
(63 reviews)

Beautiful Retreat Located in Rock Hall - walk to everything!

Rock Hall

13% off
AU$3,744
for 7 nights, 1 home
AU$535 per night
includes taxes & fees
Beautiful Retreat Located in Rock Hall - walk to everything!
Room
Exterior
Living area
Living area
Exceptional
(25 reviews)

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

Rock Hall

8% off
AU$2,474
for 7 nights, 1 home
AU$353 per night
includes taxes & fees
In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!
Dining
Pool
Screen porch for relaxing, eating, watching the water, working on a laptop
Exterior
Exceptional
(59 reviews)

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

Annapolis

16% off
AU$4,729
for 7 nights, 1 home
AU$676 per night
includes taxes & fees
Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!
Living area
Exterior
Exterior
Interior
Exceptional
(68 reviews)

Brand New Cottage Steps from the Beach!

Rock Hall

8% off
AU$2,681
for 7 nights, 1 home
AU$383 per night
includes taxes & fees
Brand New Cottage Steps from the Beach!
Living area
Terrace/patio
Exterior
Interior
Exceptional
(9 reviews)

Brand New Modern Rock Hall home with Water Views

Rock Hall

8% off
AU$3,416
for 7 nights, 1 home
AU$488 per night
includes taxes & fees
Brand New Modern Rock Hall home with Water Views
Private kitchen
Pool
Outdoor dining
Interior
Exceptional
(217 reviews)

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

Stevensville

12% off
AU$4,574
for 7 nights, 1 room
AU$653 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Outdoor dining
Exterior
Interior
Private kitchen
Exceptional
(11 reviews)

Cute waterfront apartment -- 8 min from the beach!

Rock Hall

8% off
AU$2,378
for 7 nights, 1 apartment
AU$340 per night
includes taxes & fees
Cute waterfront apartment -- 8 min from the beach!
Private kitchen
Outdoor dining
Room
Interior
Exceptional
(57 reviews)

Historic Downtown Garden Oasis with Private Patio

Chestertown

17% off
AU$1,844
for 7 nights, 1 apartment
AU$263 per night
includes taxes & fees
Historic Downtown Garden Oasis with Private Patio
main floor porch
living room w Tv and door to porch
Apartment above the Hickory Store
upper floor bedroom with 2 queen beds
Exceptional
(14 reviews)

Knot's Landing, spacious Apt. downtown Rock Hall

Rock Hall

8% off
AU$2,363
for 7 nights, 1 apartment
AU$338 per night
includes taxes & fees
Knot's Landing, spacious Apt. downtown Rock Hall

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 Stayz, 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. Stayz 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 Stayz 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 Stayz 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, Stayz 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 Stayz.
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 Stayz.
How old do you have to be to rent a holiday home in Kent County?
The minimum age allowed can differ between properties on Stayz, 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.

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