Holiday Rentals Kennedyville : Find Short-Term Rentals & Holiday Accommodations

Q: What are some of the best holiday rentals that Kennedyville has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay : This holiday home rental outside of Kennedyville is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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Our top choices for Kennedyville holiday rentals

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

1. Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Riley B.

includes taxes & fees

29 Sept - 30 Sept

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

2. First Floor Studio Apartment in Historic Chestertown

Chestertown

"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"

Charr

includes taxes & fees

29 Sept - 30 Sept

A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

3. Beachcomber Suite

Kent County

"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...

Lisa E.

includes taxes & fees

29 Sept - 30 Sept

A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

Chestertown

"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...

Miriam G.

includes taxes & fees

5 Oct - 6 Oct

A hallway with wooden flooring, a door on the right, and a window at the end.

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

Chestertown

Mandy D.

includes taxes & fees

29 Sept - 30 Sept

A wooden cabin with a porch, surrounded by dense forest.

12. Country Get Away Studio Apartment

Elkton

JAMES V.

includes taxes & fees

5 Oct - 6 Oct

A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

13. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

Aberdeen

Matthew

includes taxes & fees

29 Sept - 30 Sept

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.

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

Aberdeen

christine

includes taxes & fees

29 Sept - 30 Sept

A building with a gabled roof and a circular vent on the roof.

15. BAYSIDE BUNGALOW

Rock Hall

Diane V.

includes taxes & fees

29 Sept - 30 Sept

A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

16. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Port Deposit

Terry R S.

includes taxes & fees

29 Sept - 30 Sept

17. Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Port Deposit

Don S.

includes taxes & fees

29 Sept - 30 Sept

A bunk bed room with white bedding and blue throw blankets.

18. Bohemia Manor Farm

Chesapeake City

includes taxes & fees

13 Oct - 14 Oct

A kitchen with white cabinets, a wooden countertop, a built-in oven, and a window.

19. Quarry Landing - Center of Town & River View - 3 Bedroom

Port Deposit

jerel p.

includes taxes & fees

29 Sept - 30 Sept

A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

20. Bayside Cottage steps from Rock Hall Harbor

Rock Hall

Adam S.

includes taxes & fees

29 Sept - 30 Sept

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Everything you need to know about Kennedyville 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 Kennedyville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Kennedyville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kennedyville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kennedyville. 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 Kennedyville 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 Kennedyville holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kennedyville rentals

At Expedia, we put the best Kennedyville 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 Kennedyville 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 Kennedyville 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 Kennedyville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a holiday rental in Kennedyville?

Yes, there are holiday rentals close to the most popular sights in Kennedyville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Kennedyville has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Kennedyville is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

What’s there to see and do in Kennedyville?

Turner Creek Landing Park and Turner's Creek Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Crow Farm and Vineyard and Kent Museum.

What’s a holiday rental in Kennedyville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kennedyville. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Kennedyville holiday rentals

1. Guest Suite for up to 2 in a Victorian on the Chester River