Kennedyville Vacation Rentals

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Check prices for these dates

Tonight
Jul 28 - Jul 29
Tomorrow
Jul 29 - Jul 30
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Vacation Rentals in Kennedyville

Chesapeake Bay House with Dock & Private Beach
Relax on the lakeside deck with a round table and four Adirondack chairs, surrounded by a rocky shoreline and a wooden pier.

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (165)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Guests can enjoy a serene lakeside experience from this picturesque pier, featuring a table and chair for a peaceful retreat.

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (6)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Charming 2-bedroom cabin close to Fair Hill on horse farm
Interior

Charming 2-bedroom cabin close to Fair Hill on horse farm

9.2 out of 10, Wonderful, (5)
$590 nightly
The price is $625
Jul 30 - Jul 31
Total includes taxes and fees
Charming 2-bedroom cabin close to Fair Hill on horse farm
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Cozy living space with a comfortable sofa, desk, and storage area.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

10.0 out of 10, Exceptional, (15)
"Was a charming place to stay close to everything"
$200 nightly
The price is $211
Aug 3 - Aug 4
Total includes taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Nancy’s Touch, A Waterfront Paradise!
Stroll through the serene garden, featuring a picturesque arborway, vibrant flowers, and a birdhouse, surrounded by a tranquil body of water.

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (165)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
Nancy’s Touch, A Waterfront Paradise!
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Enjoy a meal with a view of the ocean from this dining area with large windows.

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (6)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
BAYSIDE BUNGALOW
Relax in a serene sauna with a wooden bench and natural ambiance.

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (42)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
$283 nightly
The price is $300
Jul 29 - Jul 30
Total includes taxes and fees
BAYSIDE BUNGALOW
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Guests can enjoy a serene waterfront experience with access to a marina featuring a variety of boats.

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (30)
"Our group had a great time on the Docside Doghouse. The communication with property owners was excellent and the property was exactly as advertised. Location is ideal"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
First Floor Studio Apartment in Historic Chestertown
Relax by the pool surrounded by a tranquil golf course view.

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (91)
"Very pretty location. Few minutes drive to town center."
$144 nightly
The price is $159
Aug 4 - Aug 5
Total includes taxes and fees
First Floor Studio Apartment in Historic Chestertown
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Escape to a serene cabin surrounded by lush greenery and natural beauty.

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (5)
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Enjoy a serene beach experience with access to the ocean via the public pier.

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Relax in a serene hot tub surrounded by lush greenery and a tranquil view.

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (83)
"Great place for a quick getaway - enough room for our family of 4 plus a dog to stay comfortably. Beautiful views! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Relax in a serene backyard oasis with Adirondack chairs, a table, and a chair, surrounded by a fence.

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (59)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Relax in this stylish living room with a large sofa, armchair, and ottoman, perfect for unwinding in comfort.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (53)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Kitchen area with a stove, dishwasher, refrigerator, sink, and countertop with a kettle.

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (102)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Relax in this inviting living space with a comfortable sofa, a cozy bed, and a peaceful atmosphere.

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (8)
"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Historic Chesapeake City Stay
Enjoy waterfront views from the dock and outdoor seating area, situated near a scenic bridge and lush green surroundings.

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (11)
"Always a nice get away…."
$263 nightly
The price is $279
Jul 29 - Jul 30
Total includes taxes and fees
Historic Chesapeake City Stay
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Relax in a serene hot tub under a covered pergola with a breathtaking view of the surrounding landscape.

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

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
$420 nightly
The price is $445
Jul 29 - Jul 30
Total includes taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Relax in a serene beach setting with a tranquil gazebo overlooking the ocean.

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (10)
"Perfection"
$258 nightly
The price is $285
Jul 29 - Jul 30
Total includes taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Nature's Haven Tiny Home
Enjoy al fresco dining and relaxation on this serene outdoor deck with a barbecue grill and comfortable seating.

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (2)
"Enjoyed"
$226 nightly
The price is $235
Jul 29 - Jul 30
Total includes taxes and fees
Nature's Haven Tiny 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

Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

10/10 Excellent
"Awesome activity such as slides for the kids in the pool area, kids had a blast."
Falina 3-night trip
Posted 3 days ago
Great Wolf Lodge Perryville

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.