Kennedyville Vacation Rentals

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Check prices for these dates

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

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.
The price is ￥10,930
￥17,379 total
includes taxes & fees
Jan 27 - Jan 28, 2026
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.
The price is ￥12,682
￥38,669 total
includes taxes & fees
Dec 29 - Dec 30
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.
The price is ￥15,458
￥24,801 total
includes taxes & fees
Jan 1 - Jan 2, 2026
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.
The price is ￥10,618
￥19,530 total
includes taxes & fees
Jan 27 - Jan 28, 2026
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
The price is ￥28,183
￥52,445 total
includes taxes & fees
Dec 28 - Dec 29
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.
The price is ￥21,920
￥40,330 total
includes taxes & fees
Dec 29 - Dec 30
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.
The price is ￥21,137
￥42,985 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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.
The price is ￥27,478
￥32,446 total
includes taxes & fees
Jan 1 - Jan 2, 2026
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
The price is ￥12,651
￥20,049 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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.
The price is ￥50,588
￥94,119 total
includes taxes & fees
Dec 29 - Dec 30
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.
The price is ￥27,400
￥48,759 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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.
The price is ￥23,172
￥36,180 total
includes taxes & fees
Jan 12 - Jan 13, 2026
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.
The price is ￥28,183
￥54,972 total
includes taxes & fees
Dec 28 - Dec 29
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
The price is ￥28,183
￥42,487 total
includes taxes & fees
Jan 19 - Jan 20, 2026
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
The price is ￥10,913
￥33,641 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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.
The price is ￥30,860
￥69,722 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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.
The price is ￥62,456
￥91,966 total
includes taxes & fees
Jan 27 - Jan 28, 2026
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.
The price is ￥36,356
￥169,569 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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.
The price is ￥51,028
￥78,874 total
includes taxes & fees
Jan 7 - Jan 8, 2026
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.
The price is ￥17,810
￥46,274 total
includes taxes & fees
Jan 19 - Jan 20, 2026
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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"The omelet was tasty."
Nancy 1-night trip
Posted 4 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South

Find out more about Kennedyville

Search for holiday rentals in Kennedyville on Expedia! You can easily find your home rentals, villas, holiday apartments in Kennedyville using one of the methods below:

  • View our selection of featured holiday rentals in Kennedyville
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Look no further and take a look at our great range of rental properties in Kennedyville!

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.