Kennedyville Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Oct 31 - Nov 2
In one month
Nov 14 - Nov 16
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11

Vacation Rentals in Kennedyville

Outdoor dining
Chesapeake Bay House with Dock & Private Beach
Chesapeake Bay House with Dock & Private Beach
10.0 out of 10, Exceptional, (174)
"Nice property. Large enough for 13. Plenty of space to spread out "
Chesapeake Bay House with Dock & Private Beach
Terrace/patio
Waterfront house with amazing views. Top of the Chesapeake
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (100)
"The river house has an absolutely amazing view! My kids were thrilled with the chance to fish off a very long dock and even get their feet in the water on a small beach below the house (when the tide was out). Overall, the house was perfect and just big enough for our large family of seven. Matt was very responsive to a few questions I had and was a wonderful host! "
Waterfront house with amazing views. Top of the Chesapeake
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (16)
"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! "
$265 nightly
The price is $293
Oct 21 - Oct 22
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (27)
"Very nice cottage, as advertised"
$197 nightly
The price is $208
Oct 21 - Oct 22
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Property grounds
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
9.8 out of 10, Exceptional, (11)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Terrace/patio
Nancy’s Touch, A Waterfront Paradise!
Nancy’s Touch, A Waterfront Paradise!
10.0 out of 10, Exceptional, (171)
"The house was quaint, scenic, well maintained and in a great location with a breathtaking view of the bay. We had a wonderful time there, would definitely recommend it and would love to revisit again. "
Nancy’s Touch, A Waterfront Paradise!
Fridge, microwave, oven, stovetop
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
9.8 out of 10, Exceptional, (50)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Marina
Waterfront Oasis w/ Private Dock, 3BR/2BA
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.4 out of 10, Exceptional, (36)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA
Indoor pool
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
10.0 out of 10, Exceptional, (13)
"We had such a relaxing time here! Absolutely beautiful location and property. Lots of fun on the river and in the pool. Owners were fantastic and quick to respond. Very sweet arrival basket for us with all things Maryland! "
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Marina
Historic Chesapeake City Stay
Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
$263 nightly
The price is $279
Oct 17 - Oct 18
Total with taxes and fees
Historic Chesapeake City Stay
Interior
Charming 2-bedroom cabin close to Fair Hill on horse farm
Charming 2-bedroom cabin close to Fair Hill on horse farm
9.6 out of 10, Exceptional, (8)
"Good experience"
Charming 2-bedroom cabin close to Fair Hill on horse farm
Smart TV, books
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Spa
Stunning waterfront villa with indoor pool and kids swing set and play area.
Stunning waterfront villa with indoor pool and kids swing set and play area.
9.8 out of 10, Exceptional, (19)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
Stunning waterfront villa with indoor pool and kids swing set and play area.
Outdoor dining
BAYSIDE BUNGALOW
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (51)
"Very quaint and quiet place to stay. Very relaxing."
$260 nightly
The price is $276
Oct 18 - Oct 19
Total with taxes and fees
BAYSIDE BUNGALOW
Exterior
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
9.8 out of 10, Exceptional, (94)
"The properly is in great shape, clean and well provisioned. The flat back yard is perfect for yard games and when the tide is low, there a little private beach! The kids played in the sand and floated around Still Pound Creek all weekend. Loretta was an excellent host!"
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown
5-bedroom vacation home 5 minutes from historic Charlestown
9.8 out of 10, Exceptional, (145)
"Beautiful location. Excellent accommodations. Very clean and well equipped. The only downside would be all the stones that are on the beach but if you bring beach shoes, you can get past that then it’s a Sandy beach all the way out. We would definitely come again."
$567 nightly
The price is $601
Oct 20 - Oct 21
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
Beach
Waterfront Retreat with Private Dock and Beach
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
$282 nightly
The price is $311
Oct 23 - Oct 24
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Fridge, microwave, oven, stovetop
Tiny Home Tranquil Oasis
Tiny Home Tranquil Oasis
$233 nightly
The price is $242
Oct 17 - Oct 18
Total with taxes and fees
Tiny Home Tranquil Oasis
Fridge, microwave, oven, stovetop
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, (42)
"The house was perfect for 6 young adults! We were only 5 minutes from Anchor Marina which was perfect for our group. The fire pit and outdoor set up was nice and we had plenty of space for everyone. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Marina
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.4 out of 10, Exceptional, (33)
"We loved our stay. Our family wants us to book again next year. Thank you"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kennedyville Hotel Reviews

Comfort Inn and Suites

Comfort Inn and Suites

10/10 Excellent
"Would like more options for breakfast such as eggs , bacon, fresh fruit. The fruit did not look fresh."
Velynn 1-night trip
Posted 1 day ago
Comfort Inn and Suites

Find out more about Kennedyville

Everything you need to know about Kennedyville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kennedyville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kennedyville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Kennedyville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $208 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kennedyville rentals

At Expedia, we put the best Kennedyville vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Kennedyville?

Yes, there are vacation rentals close to top local attractions in Kennedyville, or you can select a more secluded option if you're looking for a relaxing stay.

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

Chesapeake Bay House with Dock & Private Beach: This vacation home rental near Kennedyville is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 vacation rental in Kennedyville like?

Vacation rentals are private properties where you can stay for a long or short time in Kennedyville. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.