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

In two weeks
In two months
In three months
In four months

Holiday Rentals in Kennedyville

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

Port Deposit
10.0 out of 10, Exceptional, (31)
"Wow such a wonderful place, clean, warm, and full of everything you need."
United States
Oswaldo S.
The price is AU$319
includes taxes & fees
9 Dec - 10 Dec
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Perryville
10.0 out of 10, Exceptional, (20)
"Great waterfront home with sunset views! Plenty of space for our group, very clean, and the hot tub was a perfect bonus. Peaceful, relaxing, and just as described. We’d definitely come back!"
United States
Kaylyn G.
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Luxury Waterfront Home Built for Entertaining!

Abingdon
8.4 out of 10, Very good, (6)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
The price is AU$1,265
includes taxes & fees
9 Dec - 10 Dec
Luxury Waterfront Home Built for Entertaining!

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 AU$460
includes taxes & fees
1 Jan - 2 Jan 2026
BAYSIDE BUNGALOW

200 steps to the beach!

Rock Hall
10.0 out of 10, Exceptional, (93)
"Beautiful, comfortable home in a great location. "
United States
Stephanie C.
200 steps to the beach!

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
9.8 out of 10, Exceptional, (59)
"We had an amazing weekend at the cottage. It’s very clean and beautiful! The close walk to the beach is perfect and we had great weather. Would love to stay here again! "
United States
Angela F.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Elkton
9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Chesapeake Bay House with Dock & Private Beach

Elkton
10.0 out of 10, Exceptional, (178)
"We loved this house and had the best time!!"
United States
Laura C.
Chesapeake Bay House with Dock & Private Beach

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton
9.8 out of 10, Exceptional, (44)
"This was our second time staying here and we really love it! It has everything needed and is very close &convenient to any outing we did, The house layout works great for our group of six. Already planning our next trip!! "
United States
Susan G.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Charming 2-bedroom cabin close to Fair Hill on horse farm

Elkton
9.6 out of 10, Exceptional, (14)
"Excellent stay! "
United States
Edward S.
Charming 2-bedroom cabin close to Fair Hill on horse farm

Stunning waterfront villa with indoor pool and kids swing set and play area.

Earleville
9.8 out of 10, Exceptional, (20)
"Had a good time, grandkids never came out of the pool"
United States
Michael D.
Stunning waterfront villa with indoor pool and kids swing set and play area.

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville
9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is AU$915
includes taxes & fees
10 Dec - 11 Dec
5-bedroom vacation home 5 minutes from historic Charlestown

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 AU$429
includes taxes & fees
5 Jan - 6 Jan 2026
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Tiny Home Tranquil Oasis

Bear
Tiny Home Tranquil Oasis

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown
10.0 out of 10, Exceptional, (12)
"Kayaks were a great plus! Ideal spot for a small family with easy access to the the beautiful Chester River. Our grandchildren had a blast, visiting the pigs, chickens, and sheep that were within easy walking distance."
United States
Douglas N.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

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 AU$2,048
includes taxes & fees
9 Dec - 10 Dec
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (19)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is AU$424
includes taxes & fees
9 Dec - 10 Dec
Historic Chesapeake City Stay

Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Chesapeake City
10.0 out of 10, Exceptional, (72)
"Great house close to canal and downtown Chesapeake City!"
United States
Michael M.
Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is AU$242
includes taxes & fees
9 Dec - 10 Dec
First Floor Studio Apartment in Historic Chestertown

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

Port Deposit
10.0 out of 10, Exceptional, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is AU$354
includes taxes & fees
5 Jan - 6 Jan 2026
Quarry Landing - Center of Town & River View - 3 Bedroom
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 favourite 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 depend 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 AU$242 per night. Entering your travel dates in the search wizard might find you 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?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This holiday home rental outside of Kennedyville is located on a river, and has a patio, a garden 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 can relax into your holiday 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.