Kennedyville Vacation Rentals

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Our top choices for Kennedyville vacation rentals

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
9.6 out of 10, Exceptional, (19 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is CA $93
CA $171 total
includes taxes & fees
Feb 9 - Feb 10
Guest Suite for up to 2 in a Victorian on the Chester River

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"The accommodation description is good; the actual accommodations are great, better than expected, truly a quiet country getaway with many unexpected extras. Deciding to stay here was great decision. It's done right."
United States
John L.
The price is CA $96
CA $152 total
includes taxes & fees
Feb 16 - Feb 17
Country Get Away 1 Bedroom Apartment

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
8.0 out of 10, Very good, (12 reviews)
"Pleasant stay"
United States
Yommali G.
The price is CA $92
CA $127 total
includes taxes & fees
Feb 9 - Feb 10
Charming 2-bedroom house in Aberdeen with WiFi and AC

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

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is CA $182
CA $293 total
includes taxes & fees
Feb 10 - Feb 11
Quarry Landing - Center of Town & River View - 3 Bedroom

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"Yes she was welcoming "
United States
Garry B.
The price is CA $148
CA $383 total
includes taxes & fees
Feb 12 - Feb 13
Historic Chesapeake City Stay

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

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
10.0 out of 10, Exceptional, (35 reviews)
"Very cool place. "
United States
Eric L.
The price is CA $240
CA $288 total
includes taxes & fees
Feb 9 - Feb 10
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Hobbit House one of a kind home

Hobbit House one of a kind home
Bel Air
10.0 out of 10, Exceptional, (9 reviews)
"We had a great stay! "
United States
Courtney H.
The price is CA $128
CA $383 total
includes taxes & fees
Feb 9 - Feb 10
Hobbit House one of a kind home

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is CA $135
CA $217 total
includes taxes & fees
Feb 9 - Feb 10
First Floor Studio Apartment in Historic Chestertown

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, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is CA $161
CA $392 total
includes taxes & fees
Feb 9 - Feb 10
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Elkton
8.6 out of 10, Excellent, (14 reviews)
"Nice and quiet place to stay"
United States
Gary M.
The price is CA $185
CA $388 total
includes taxes & fees
Feb 9 - Feb 10
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

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

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Chesapeake City
9.4 out of 10, Exceptional, (3 reviews)
"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 CA $239
CA $454 total
includes taxes & fees
Mar 1 - Mar 2
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.2 out of 10, Wonderful, (9 reviews)
"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 CA $148
CA $369 total
includes taxes & fees
Feb 9 - Feb 10
Amazing Modern house with a full kitchen and parking

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is CA $239
CA $430 total
includes taxes & fees
Feb 9 - Feb 10
Waterfront Retreat with Private Dock and Beach

Spacious Private 2BR Suite in Abingdon with Separate Entrance

Spacious Private 2BR Suite in Abingdon with Separate Entrance
Bel Air South
The price is CA $108
CA $173 total
includes taxes & fees
Feb 9 - Feb 10
Spacious Private 2BR Suite in Abingdon with Separate Entrance

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (5 reviews)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
The price is CA $344
CA $573 total
includes taxes & fees
Feb 9 - Feb 10
Long Beach Cottage, (romantic couple’s getaway)

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is CA $237
CA $277 total
includes taxes & fees
Feb 27 - Feb 28
High Tide Haven Suite

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

Grandma’s Cottage will wrap around you like a warm hug
Betterton
The price is CA $308
CA $577 total
includes taxes & fees
Feb 9 - Feb 10
Grandma’s Cottage will wrap around you like a warm hug

Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater
Middletown
The price is CA $70
CA $612 total
includes taxes & fees
Feb 9 - Feb 10
Heated Pool • Private Backyard • Home Theater

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1 review)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is CA $547
CA $803 total
includes taxes & fees
Feb 14 - Feb 15
JVA LUXURY HOUSING

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (147 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is CA $353
CA $724 total
includes taxes & fees
Feb 9 - Feb 10
5-bedroom vacation home 5 minutes from historic Charlestown
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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Top Kennedyville Hotel Reviews

Find out more about Kennedyville

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kennedyville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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

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.