Kennedyville Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Kennedyville

Country Get Away 1 Bedroom Apartment

Elkton
9.8 out of 10, Exceptional, (40)
"Perfect in every way… a great stay"
United States
Robert B.
The price is NZ$196
includes taxes & fees
1 Dec - 2 Dec
Country Get Away 1 Bedroom Apartment

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

Millington
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is NZ$220
includes taxes & fees
19 Nov - 20 Nov
Guest Suite for up to 2 in a Victorian on the Chester River

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

2.0 star property
Chesapeake City
9.4 out of 10, Exceptional, (3)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is NZ$589
includes taxes & fees
19 Nov - 20 Nov
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Small House on Gentleman’s Farm

Bel Air
10.0 out of 10, Exceptional, (12)
"Wonderful property located in a peaceful setting. This is our next stay at the Gentlemen’s Farm. Pastoral location that is convenient to Bel Air. House is so clean and well maintained. We had everything available that we needed. Tracey is so responsive in providing information that makes the stay even better. We will stay here again when in the area visiting family."
United States
Jim S.
The price is NZ$521
includes taxes & fees
3 Dec - 4 Dec
Small House on Gentleman’s Farm

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (18)
"The property was clean and simply appointed w just the bare essentials for a short stay. Location was convenient for our purposes and the host was communicative"
United States
Melvin P.
The price is NZ$491
includes taxes & fees
19 Nov - 20 Nov
Historic Chesapeake City Stay

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

Port Deposit
10.0 out of 10, Exceptional, (30)
"Wow such a wonderful place, clean, warm, and full of everything you need."
United States
Oswaldo S.
The price is NZ$370
includes taxes & fees
19 Nov - 20 Nov
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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

Port Deposit
10.0 out of 10, Exceptional, (11)
"Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙"
United States
Elise E.
The price is NZ$410
includes taxes & fees
3 Dec - 4 Dec
Quarry Landing - Center of Town & River View - 3 Bedroom

Long Beach Cottage, (romantic couple’s getaway)

Charlestown
10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
The price is NZ$844
includes taxes & fees
30 Nov - 1 Dec
Long Beach Cottage, (romantic couple’s getaway)

JVA LUXURY HOUSING

Smyrna
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is NZ$1,037
includes taxes & fees
24 Nov - 25 Nov
JVA LUXURY HOUSING

Sparkling new! A Craftsman-style cottage in the heart of Rock Hall

Rock Hall
10.0 out of 10, Exceptional, (2)
"I spent a wonderful 8 nights at the Dragonfly Cottage in the quaint bayside town of Rock Hall. The cottage was in a prime location and perfectly situated for long morning walks around the town. The cottage itself is brand new with every accommodation you can think of to have a comfortable stay. The 3 large bedrooms and open floor plan kitchen / living area provide plenty of space to spread out. Everything was sparkling clean and you can tell the hosts have taken a lot of care to anticipate your...
United States
Alison F.
Sparkling new! A Craftsman-style cottage in the heart of Rock Hall

Amazing Modern house with a full kitchen and parking

Smyrna
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is NZ$628
includes taxes & fees
19 Nov - 20 Nov
Amazing Modern house with a full kitchen and parking

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (106)
"Amazing and neat and very private "
United States
Alexander M.
The price is NZ$280
includes taxes & fees
20 Nov - 21 Nov
First Floor Studio Apartment in Historic Chestertown

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is NZ$526
includes taxes & fees
24 Nov - 25 Nov
BAYSIDE BUNGALOW

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is NZ$479
includes taxes & fees
24 Nov - 25 Nov
Chesapeake Bay Harbor View in a central location to events/restaurants

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall
10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is NZ$504
includes taxes & fees
19 Nov - 20 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Chesapeake Bay Retreat W/Breathtaking Views

Rock Hall
10.0 out of 10, Exceptional, (1)
"Beautiful home situated right on the water with everything we could need. Would not hesitate to return! "
United States
josh b.
The price is NZ$1,410
includes taxes & fees
1 Dec - 2 Dec
Chesapeake Bay Retreat W/Breathtaking Views

Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Bel Air
10.0 out of 10, Exceptional, (5)
"I appreciated how clean and pleasant it smelled! Then it was a beautiful location with lots of places to eat nearby. My only improvement would have been window curtains, especially in the master bath. "
United States
Leah M.
The price is NZ$586
includes taxes & fees
1 Dec - 2 Dec
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Havre de Grace
9.8 out of 10, Exceptional, (6)
"Beautiful home and property. The house was clean and welcoming and the pool was an absolute delight. Would definitely stay again! "
United States
Julia B.
The price is NZ$2,362
includes taxes & fees
23 Nov - 24 Nov
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Private 3 room Queen Suite w/Kitchenette

Port Deposit
10.0 out of 10, Exceptional, (29)
"Perfect location for that town. "
United States
Hisham M.
The price is NZ$453
includes taxes & fees
19 Nov - 20 Nov
Private 3 room Queen Suite w/Kitchenette

Grandma’s Cottage will wrap around you like a warm hug

Betterton
The price is NZ$741
includes taxes & fees
19 Nov - 20 Nov
Grandma’s Cottage will wrap around you like a warm hug
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Kennedyville Hotel Reviews

Find out more about Kennedyville

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, 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 NZ$280 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?

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Kennedyville is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.