Kent County Holiday Rentals

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Top cities in Kent County

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

Chestertown

Chestertown

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Kent County holiday 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, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is NZ$271
includes taxes & fees
10 Nov - 11 Nov
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, (34 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 NZ$603
includes taxes & fees
10 Nov - 11 Nov
Newly restored apartment in the heart of Chestertown
A garden with a wooden bridge, lush greenery, and a variety of plants.

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.
The price is NZ$492
includes taxes & fees
10 Nov - 11 Nov
Secluded Cottage in Middle of Chestertown
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

4. 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 NZ$210
includes taxes & fees
10 Nov - 11 Nov
Guest Suite for up to 2 in a Victorian on the Chester River
A covered porch with a wooden bench, potted plants, and a decorative railing.

5. 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, (76 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is NZ$815
includes taxes & fees
10 Nov - 11 Nov
Wren Retweet- Country Estate in Center of C’Town
A building with a gabled roof and a circular vent on the roof.

6. 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 NZ$539
includes taxes & fees
10 Nov - 11 Nov
BAYSIDE BUNGALOW
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

7. 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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is NZ$506
includes taxes & fees
12 Nov - 13 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

8. 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 NZ$341
includes taxes & fees
23 Nov - 24 Nov
Turtle Cove Room
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.
The price is NZ$356
includes taxes & fees
23 Nov - 24 Nov
Beachcomber Suite
A wooden staircase leading to a beach with a clear view of the sea.

10. 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 NZ$618
includes taxes & fees
30 Nov - 1 Dec
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
A kitchen with wooden cabinets, a dining table, and a refrigerator.

11. 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 NZ$514
includes taxes & fees
10 Nov - 11 Nov
Family Retreat at Lansdowne Manor
A deck with a view of a marina, including boats and docks.

12. 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 NZ$463
includes taxes & fees
12 Nov - 13 Nov
Cass-N-Reel Luxury Houseboat
A courtyard with brick flooring, wicker furniture, and a fire pit.

13. 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 NZ$613
includes taxes & fees
11 Nov - 12 Nov
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, (50 reviews)
"Great stay"
United States
Michael V.
The price is NZ$497
includes taxes & fees
10 Nov - 11 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

15. 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 NZ$262
includes taxes & fees
11 Nov - 12 Nov
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A riverside dock with boats, a covered seating area, and a bridge in the background.

16. 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 NZ$537
includes taxes & fees
10 Nov - 11 Nov
Historic Chesapeake City Stay
Restaurant

17. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is NZ$987
includes taxes & fees
19 Nov - 20 Nov
Bohemia Manor Farm
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

18. 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 NZ$547
includes taxes & fees
15 Nov - 16 Nov
Relax on Kent Island in 4 Bedroom Home w/Waterview
An outdoor seating area with tables and chairs, umbrellas, and a view of the water.

19. 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 NZ$2,236
includes taxes & fees
1 Dec - 2 Dec
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

20. 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 NZ$828
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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Find holiday rentals that suit your style

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Top Kent County Hotel Reviews

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville

10/10 Excellent

Can’t fault this hotel. The location is amazing. Rooms were roomy and clean with everything you need. Had some food in the restaurant which was really nice. The view from the patio is amazing. Breakfast options were better than we had seen in most hotels. Staff were lovely
Australia
Gayle
Reviewed July 9, 2024
Hyatt Place Kent Narrows & Marina

Find out more about Kent County

Everything you need to know about Kent County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kent County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kent County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kent County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kent County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kent County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kent County holiday rentals we have selected for you start as low as NZ$152 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kent County rentals

At Expedia, we put the best Kent County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kent County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kent County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kent County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.