Kennedyville Holiday Rentals

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Check prices for these dates

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Kennedyville holiday 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 HK$544
HK$865 total
includes taxes & fees
5 Jan - 6 Jan 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 HK$629
HK$1,919 total
includes taxes & fees
30 Dec - 31 Dec
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 HK$769
HK$1,234 total
includes taxes & fees
30 Dec - 31 Dec
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 HK$528
HK$972 total
includes taxes & fees
31 Dec - 1 Jan 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 HK$1,399
HK$2,603 total
includes taxes & fees
30 Dec - 31 Dec
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 HK$1,088
HK$2,002 total
includes taxes & fees
5 Jan - 6 Jan 2026
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 HK$1,049
HK$2,134 total
includes taxes & fees
4 Jan - 5 Jan 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 HK$1,364
HK$1,610 total
includes taxes & fees
1 Jan - 2 Jan 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 HK$628
HK$995 total
includes taxes & fees
4 Jan - 5 Jan 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 HK$2,511
HK$4,672 total
includes taxes & fees
1 Jan - 2 Jan 2026
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 HK$1,360
HK$2,420 total
includes taxes & fees
6 Jan - 7 Jan 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 HK$1,150
HK$1,796 total
includes taxes & fees
12 Jan - 13 Jan 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 HK$1,399
HK$2,760 total
includes taxes & fees
30 Dec - 31 Dec
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 HK$1,554
HK$2,348 total
includes taxes & fees
1 Jan - 2 Jan 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 HK$542
HK$1,670 total
includes taxes & fees
4 Jan - 5 Jan 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 HK$1,532
HK$3,461 total
includes taxes & fees
5 Jan - 6 Jan 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 HK$3,109
HK$4,546 total
includes taxes & fees
5 Jan - 6 Jan 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 HK$1,805
HK$8,867 total
includes taxes & fees
5 Jan - 6 Jan 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 HK$2,533
HK$3,915 total
includes taxes & fees
7 Jan - 8 Jan 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 HK$865
HK$2,269 total
includes taxes & fees
20 Jan - 21 Jan 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

Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen

10/10 Excellent
"Good ac"
NANCY 1-night trip
Posted 2 days ago
Days Inn by Wyndham Aberdeen

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
  • Use the map to find apartments and other holiday homes in the Kennedyville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Kennedyville while they last

Look no further and take a look at our great range of rental properties in Kennedyville!

Frequently asked questions

Can I find a holiday rental in Kennedyville?

Yes, there are holiday rentals close to the most popular sights in Kennedyville, or you can select a more secluded option if you're looking for a relaxing stay.

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

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Kennedyville is located on the beach, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 holiday rental in Kennedyville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kennedyville. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.