Kennedyville Holiday Rentals

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Our top choices for Kennedyville holiday rentals

Cabin in Chesapeake City

Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (20 reviews)
"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 NZ$461
includes taxes & fees
2 Mar - 3 Mar
Historic Chesapeake City Stay
9.6 out of 10, Exceptional, (108 reviews)
"Everything was clean and neat and welcoming "
United States
Iriana J.
The price is NZ$265
includes taxes & fees
5 Mar - 6 Mar
First Floor Studio Apartment in Historic Chestertown
10.0 out of 10, Exceptional, (38 reviews)
"Very cool place. "
United States
Eric L.
The price is NZ$347
includes taxes & fees
5 Mar - 6 Mar
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
9.8 out of 10, Exceptional, (40 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is NZ$186
includes taxes & fees
9 Mar - 10 Mar
Country Get Away 1 Bedroom Apartment
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 NZ$830
includes taxes & fees
4 Mar - 5 Mar
Long Beach Cottage, (romantic couple’s getaway)
10.0 out of 10, Exceptional, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is NZ$359
includes taxes & fees
2 Mar - 3 Mar
Quarry Landing - Center of Town & River View - 3 Bedroom
8.0 out of 10, Very good, (12 reviews)
"Pleasant stay"
United States
Yommali G.
The price is NZ$156
includes taxes & fees
28 Feb - 1 Mar
Charming 2-bedroom house in Aberdeen with WiFi and AC
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 NZ$503
includes taxes & fees
1 Mar - 2 Mar
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
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 NZ$584
includes taxes & fees
1 Mar - 2 Mar
Amazing Modern house with a full kitchen and parking
10.0 out of 10, Exceptional, (5 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is NZ$320
includes taxes & fees
1 Mar - 2 Mar
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
8.6 out of 10, Excellent, (14 reviews)
"Nice and quiet place to stay"
United States
Gary M.
The price is NZ$468
includes taxes & fees
8 Mar - 9 Mar
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is NZ$210
includes taxes & fees
24 Mar - 25 Mar
Guest Suite for up to 2 in a Victorian on the Chester River
9.8 out of 10, Exceptional, (148 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 NZ$871
includes taxes & fees
2 Mar - 3 Mar
5-bedroom vacation home 5 minutes from historic Charlestown
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 NZ$517
includes taxes & fees
11 Mar - 12 Mar
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is NZ$475
includes taxes & fees
27 Feb - 28 Feb
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment in Kent County

High Tide Haven Suite
The price is NZ$333
includes taxes & fees
12 Mar - 13 Mar
High Tide Haven Suite
10.0 out of 10, Exceptional, (29 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is NZ$430
includes taxes & fees
11 Mar - 12 Mar
Private 3 room Queen Suite w/Kitchenette
The price is NZ$375
includes taxes & fees
6 Mar - 7 Mar
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
9.0 out of 10, Wonderful, (9 reviews)
"Excellent communication with host, we had everything we needed"
United States
Kelly W.
The price is NZ$1,959
includes taxes & fees
9 Mar - 10 Mar
Luxury Waterfront Home Built for Entertaining!
The price is NZ$696
includes taxes & fees
9 Mar - 10 Mar
Grandma’s Cottage will wrap around you like a warm hug
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

Everything you need to know about Kennedyville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kennedyville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kennedyville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kennedyville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kennedyville holiday rentals we have selected for you start as low as NZ$347 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kennedyville rentals

At Expedia, we put the best Kennedyville holiday 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 holiday.

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. 

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?

5-bedroom vacation home 5 minutes from historic Charlestown: This holiday home rental outside of Kennedyville is located on a river, and has a balcony, a garden 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. Make the most of games in this rental home to help you unwind.

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.