Kennedyville Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Kennedyville vacation rentals

Property grounds
Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
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 5 - Jan 6, 2026
Total with taxes and fees
Country Get Away 1 Bedroom Apartment
Marina
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
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.
$233 nightly
The price is $247
Dec 29 - Dec 30
Total with taxes and fees
Historic Chesapeake City Stay
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

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.
$144 nightly
The price is $159
Dec 29 - Dec 30
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Exterior
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

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.
$118 nightly
The price is $125
Dec 31 - Jan 1, 2026
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Fridge, microwave, oven, stovetop
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

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
$316 nightly
The price is $335
Dec 29 - Dec 30
Total with taxes and fees
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Exterior
Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette

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.
$243 nightly
The price is $258
Dec 29 - Dec 30
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette
Fridge, microwave, oven, stovetop
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

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

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Elkton
8.2 out of 10, Very Good, (12)
"Nice and quiet place to stay"
United States
Gary M.
$259 nightly
The price is $275
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
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.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
10.0 out of 10, Exceptional, (33)
"The River Cottage is very charming, cozy, and well-stocked with all the essentials. The host is quick to respond to inquiries. We had a wonderful and relaxing stay!"
United States
Xiaodong F.
$196 nightly
The price is $207
Jan 1 - Jan 2, 2026
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Microwave, oven, stovetop
Spacious Private 2BR Suite in Abingdon with Separate Entrance

Spacious Private 2BR Suite in Abingdon with Separate Entrance

Spacious Private 2BR Suite in Abingdon with Separate Entrance
2.0 star property
Bel Air South
$121 nightly
The price is $128
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spacious Private 2BR Suite in Abingdon with Separate Entrance
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

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, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
$567 nightly
The price is $601
Dec 29 - Dec 30
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

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
$282 nightly
The price is $311
Jan 6 - Jan 7, 2026
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

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)
"Was a great stay would definitely stay again "
United States
jerel p.
$201 nightly
The price is $213
Jan 13 - Jan 14, 2026
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
Dining
Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking

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.
$348 nightly
The price is $356
Dec 29 - Dec 30
Total with taxes and fees
Amazing Modern house with a full kitchen and parking
Outdoor dining
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$262 nightly
The price is $278
Jan 1 - Jan 2, 2026
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

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
$203 nightly
The price is $215
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville
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, 2026
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Private kitchen
JVA LUXURY HOUSING

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
$571 nightly
The price is $589
Jan 4 - Jan 5, 2026
Total with taxes and fees
JVA LUXURY HOUSING
Outdoor dining
Spacious 4-bedroom house with backyard oasis

Spacious 4-bedroom house with backyard oasis

Spacious 4-bedroom house with backyard oasis
Middletown
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.
$1,060 nightly
The price is $1,083
Jan 5 - Jan 6, 2026
Total with taxes and fees
Spacious 4-bedroom house with backyard oasis
Outdoor spa tub
Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)

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.
$481 nightly
The price is $504
Jan 7 - Jan 8, 2026
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
Property grounds
Hobbit House one of a kind home

Hobbit House one of a kind home

Hobbit House one of a kind home
Bel Air
10.0 out of 10, Exceptional, (8)
"We had a great stay! "
United States
Courtney H.
$290 nightly
The price is $292
Jan 19 - Jan 20, 2026
Total with taxes and fees
Hobbit House one of a kind home
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

Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen

10/10 Excellent
"Good ac"
NANCY 1-night trip
Posted 16 hours ago
Days Inn by Wyndham Aberdeen

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?

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.