Holiday Rentals in Kennedyville

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Kennedyville

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (25)
"Very nice cottage, as advertised"
The price is €182
includes taxes & fees
21 Oct - 22 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Chesapeake Bay House with Dock & Private Beach
Outdoor dining
Chesapeake Bay House with Dock & Private Beach
10.0 out of 10, Exceptional, (174)
"Nice property. Large enough for 13. Plenty of space to spread out "
Chesapeake Bay House with Dock & Private Beach
Waterfront house with amazing views. Top of the Chesapeake
Terrace/patio
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (100)
"The river house has an absolutely amazing view! My kids were thrilled with the chance to fish off a very long dock and even get their feet in the water on a small beach below the house (when the tide was out). Overall, the house was perfect and just big enough for our large family of seven. Matt was very responsive to a few questions I had and was a wonderful host! "
Waterfront house with amazing views. Top of the Chesapeake
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (16)
"Great place for our short trip anniversary getaway. Mermaid’s getaway was clean and well stocked with cookware. Rick was very communicative and made sure that we felt right at home and that we could easily contact him if there were any issues (there weren’t). Rock Hall was a charming little town."
The price is €251
includes taxes & fees
14 Oct - 15 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Nancy’s Touch, A Waterfront Paradise!
Terrace/patio
Nancy’s Touch, A Waterfront Paradise!
10.0 out of 10, Exceptional, (171)
"The house was quaint, scenic, well maintained and in a great location with a breathtaking view of the bay. We had a wonderful time there, would definitely recommend it and would love to revisit again. "
Nancy’s Touch, A Waterfront Paradise!
Historic Chesapeake City Stay
Marina
Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
The price is €246
includes taxes & fees
16 Oct - 17 Oct
Historic Chesapeake City Stay
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
9.8 out of 10, Exceptional, (50)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Waterfront Oasis w/ Private Dock, 3BR/2BA
Marina
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.4 out of 10, Exceptional, (36)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Indoor pool
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
10.0 out of 10, Exceptional, (13)
"We had such a relaxing time here! Absolutely beautiful location and property. Lots of fun on the river and in the pool. Owners were fantastic and quick to respond. Very sweet arrival basket for us with all things Maryland! "
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Stunning waterfront villa with indoor pool and kids swing set and play area.
Spa
Stunning waterfront villa with indoor pool and kids swing set and play area.
9.8 out of 10, Exceptional, (19)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
Stunning waterfront villa with indoor pool and kids swing set and play area.
Charming 2-bedroom cabin close to Fair Hill on horse farm
Interior
Charming 2-bedroom cabin close to Fair Hill on horse farm
9.6 out of 10, Exceptional, (8)
"Good experience"
Charming 2-bedroom cabin close to Fair Hill on horse farm
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
Exterior
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
9.8 out of 10, Exceptional, (94)
"The properly is in great shape, clean and well provisioned. The flat back yard is perfect for yard games and when the tide is low, there a little private beach! The kids played in the sand and floated around Still Pound Creek all weekend. Loretta was an excellent host!"
Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown
BAYSIDE BUNGALOW
Outdoor dining
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (51)
"Very quaint and quiet place to stay. Very relaxing."
The price is €239
includes taxes & fees
25 Oct - 26 Oct
BAYSIDE BUNGALOW
Waterfront Retreat with Private Dock and Beach
Beach
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
The price is €269
includes taxes & fees
27 Oct - 28 Oct
Waterfront Retreat with Private Dock and Beach
Tiny Home Tranquil Oasis
Fridge, microwave, oven, stovetop
Tiny Home Tranquil Oasis
The price is €213
includes taxes & fees
14 Oct - 15 Oct
Tiny Home Tranquil Oasis
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
10.0 out of 10, Exceptional, (10)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
5-bedroom vacation home 5 minutes from historic Charlestown
Sun-loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown
9.8 out of 10, Exceptional, (145)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is €530
includes taxes & fees
15 Oct - 16 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
Quarry Landing - Center of Town & River View - 3 Bedroom
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom
9.8 out of 10, Exceptional, (9)
"Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙"
The price is €204
includes taxes & fees
3 Nov - 4 Nov
Quarry Landing - Center of Town & River View - 3 Bedroom
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
9.6 out of 10, Exceptional, (23)
"Nice clean home, comfortable bedrooms, accommodating bathrooms and good working kitchen. Highlight is back deck leading to Chester River. You can use the kayaks at the property and fishing is very good! Overall pleasant experience and would definitely stay there again. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

10/10 Excellent
"Is good excelent"
Miguel 2-night trip
Posted 2 days ago
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

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, apart-hotels, 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 €182 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?

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.