Kennedyville Vacation Rentals

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Jan 4 - Jan 5
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Jan 9 - Jan 11
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Jan 16 - Jan 18

Our top choices for Kennedyville vacation rentals

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

Apartment in Millington

Guest Suite for up to 2 in a Victorian on the Chester River
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.
$118 nightly
The price is $125
Jan 12 - Jan 13
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds
Country Get Away 1 Bedroom Apartment

Apartment in Elkton

Country Get Away 1 Bedroom Apartment
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
$105 nightly
The price is $111
Jan 13 - Jan 14
Total with taxes and fees
Country Get Away 1 Bedroom Apartment
Marina
Historic Chesapeake City Stay

Cabin in Chesapeake City

Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (20)
"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.
$263 nightly
The price is $279
Jan 5 - Jan 6
Total with taxes and fees
Historic Chesapeake City Stay
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
$144 nightly
The price is $159
Jan 5 - Jan 6
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

Cottage in Port Deposit

Quarry Landing - Center of Town & River View - 3 Bedroom
10.0 out of 10, Exceptional, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
$201 nightly
The price is $213
Jan 12 - Jan 13
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Cottage in Port Deposit

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (34)
"What a cozy place to stay! The best part was in the morning when you can see the beautiful morning sky from the bed in the loft, the sun eloquently shining in through the windows and the deer frolicking in the yard. Comfy beds and plenty of lighting, would love to stay again."
United States
Bobbijo B.
$196 nightly
The price is $207
Jan 5 - Jan 6
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Fridge, microwave, oven, stovetop
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Apartment in Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
2.0 star property
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
$316 nightly
The price is $335
Jan 5 - Jan 6
Total with taxes and fees
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Fridge, microwave, oven, stovetop
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Vacation Home in Elkton

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
8.6 out of 10, Excellent, (14)
"Nice and quiet place to stay"
United States
Gary M.
$258 nightly
The price is $273
Jan 6 - Jan 7
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Dining
Amazing Modern house with a full kitchen and parking

Vacation Home in Smyrna

Amazing Modern house with a full kitchen and parking
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.
$349 nightly
The price is $357
Jan 8 - Jan 9
Total with taxes and fees
Amazing Modern house with a full kitchen and parking
Exterior
Private 3 room Queen Suite w/Kitchenette

Apartment in Port Deposit

Private 3 room Queen Suite w/Kitchenette
10.0 out of 10, Exceptional, (29)
"Perfect location for that town. "
United States
Hisham M.
$243 nightly
The price is $258
Jan 5 - Jan 6
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette
Microwave, oven, stovetop
Spacious Private 2BR Suite in Abingdon with Separate Entrance

Vacation Home in Bel Air South

Spacious Private 2BR Suite in Abingdon with Separate Entrance
2.0 star property
$122 nightly
The price is $130
Jan 5 - Jan 6
Total with taxes and fees
Spacious Private 2BR Suite in Abingdon with Separate Entrance
Outdoor dining
Spacious 4-bedroom house with backyard oasis

Vacation Home in Middletown

Spacious 4-bedroom house with backyard oasis
10.0 out of 10, Exceptional, (1)
"We had a nice stay at this gorgeous house! Very comfortable and nicely appointed."
United States
Jordan K.
$1,117 nightly
The price is $1,139
Jan 13 - Jan 14
Total with taxes and fees
Spacious 4-bedroom house with backyard oasis
Interior
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Vacation Home in Bel Air

Modern and Cozy Home in Bel Air with a Home Office and Fireplace
10.0 out of 10, Exceptional, (5)
"The house was even better than I anticipated! It was very clean, quiet and comfy. The beds were amazing and we got the best nights sleep! Location was perfect for Ripken Experience. The owner was very helpful and quick to respond to my messages. "
United States
Alexandra C.
$254 nightly
The price is $269
Jan 6 - Jan 7
Total with taxes and fees
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Beach
Waterfront Retreat with Private Dock and Beach

Apartment in Worton

Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (25)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
$282 nightly
The price is $311
Jan 6 - Jan 7
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Vacation Home in Centreville

HGTV quality, private guest suite, country getaway with hot tub & fire pit
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
$420 nightly
The price is $445
Jan 5 - Jan 6
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio
Grandma’s Cottage will wrap around you like a warm hug

Cottage in Betterton

Grandma’s Cottage will wrap around you like a warm hug
$398 nightly
The price is $422
Jan 5 - Jan 6
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
Property grounds
Hobbit House one of a kind home

Vacation Home in Bel Air

Hobbit House one of a kind home
10.0 out of 10, Exceptional, (8)
"We had a great stay! "
United States
Courtney H.
$296 nightly
The price is $298
Feb 2 - Feb 3
Total with taxes and fees
Hobbit House one of a kind home
Outdoor dining
BAYSIDE BUNGALOW

Vacation Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$260 nightly
The price is $276
Jan 5 - Jan 6
Total with taxes and fees
BAYSIDE BUNGALOW
1 bedroom, iron/ironing board, free WiFi, bed sheets
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Vacation Home in Aberdeen

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
$212 nightly
The price is $225
Feb 4 - Feb 5
Total with taxes and fees
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Outdoor spa tub
Long Beach Cottage, (romantic couple’s getaway)

Cottage in Charlestown

Long Beach Cottage, (romantic couple’s getaway)
10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
$397 nightly
The price is $415
Jan 7 - Jan 8
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
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

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

10/10 Excellent
"Everything was fine. I had no complaints at all about anything."
Eugenia 2-night trip
Posted 1 day ago
Fairfield Inn & Suites by Marriott Middletown

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 $159 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?

BAYSIDE BUNGALOW: This vacation home rental near Kennedyville is equipped with a patio, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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.