Holiday Homes in Kennedyville

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Featured Holiday Homes in Kennedyville

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.8 out of 10, Exceptional, (26)
"The house is spacious (more than the photos may lead you to believe), with numerous gathering centers inside and out. My guests enjoyed the dock at sunset and the fire pit by the water. The patio under the house had a charcoal grill and ample space for tables and chairs. Though our weekend had perfect weather, the covered patio made the place "weatherproof" had it rained. There is tons of parking, and a beautiful view over the water. The Host was readily available via VRBO messaging, Usually...
Waterfront Oasis w/ Private Dock, 3BR/2BA

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
10.0 out of 10, Exceptional, (1)
Pet-Friendly Home on Chester River w/ Dock!

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (22)
"The pictures dont do this rental house justice. It was very clean and wonderfully decorated. The seperate unit was ideal for my daughter and her family. The "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

10.0 out of 10, Exceptional, (48)
"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
Waterfront house with amazing views. Top of the Chesapeake

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

9.8 out of 10, Exceptional, (40)
"This cottage was very cute inside, but could use some curb appeal. When we pulled up, we were worried what the inside looked like. The front bedroom is literally in front of the door, so no one wanted to sleep in that room. The back bedroom in the sunroom, got very cold. The front door would not properly lock, and we realized that you could punch in any number to unlock it. The inside was very cute and updated, but there needs to be some repairs to justify the price. Bedroom doors did not shut...
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (33)
"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (61)
"What an amazing place... the sunsets, the house, the pool, the amenities... absolutely everything was perfect! The owner was super helpful! "
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (23)
"The property was excellent for a large group. We was there for a Sailing Regatta on the lake in front of the house. The perfect house for groups."
Waterfront family resort Lodge with private pier, game room and bar

Historic home in the heart of Main Street- walkable to shops and restaurants

10.0 out of 10, Exceptional, (9)
"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."
The price is AU$719
includes taxes & fees
9 Dec - 10 Dec
Historic home in the heart of Main Street- walkable to shops and restaurants

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (18)
"Wonderful place to stay!"
Amazing Waterfront Home on the Bush River

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

10.0 out of 10, Exceptional, (14)
"This property was great for our group of 6 adults. Plenty of space for us to hang out, comfortable rooms and beds, the kitchen had everything we needed. Unfortunately with the weather we weren’t able to use the outside much but it was very cute and looked cozy! It is a short walk to Main Street with cute shops, a grocery store and coffee shop. We all would happily come back again! "
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

7.4 out of 10, Good, (3)
"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

Sweet Little Home Away From Home, North East, MD

10.0 out of 10, Exceptional, (4)
"My family enjoyed our stay at Angela's house in North East. The house was clean, beds were comfortable, kitchen had what we needed. We'd stay there again."
Sweet Little Home Away From Home, North East, MD

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (33)
"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "
The price is AU$424
includes taxes & fees
28 Nov - 29 Nov
BAYSIDE BUNGALOW

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

9.6 out of 10, Exceptional, (35)
"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (12)
"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"
Chesapeake City Quiet Overlook

200 steps to the beach!

10.0 out of 10, Exceptional, (85)
"I enjoyed my stay. I've stayed in the house before."
200 steps to the beach!

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (7)
"More than expected. Great locatiom. Everything. But hot chocolate pods provided. Loved it"
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Langford Creek Estate | Waterfront w/ HOT TUB + Deck!

9.2 out of 10, Wonderful, (5)
"The owners were very flexible with us and understanding when it came to a booking mistake on my end. The house is lovely and the property is absolutely gorgeous. The deck was picture perfect. Highly recommend for a getaway on the eastern shore!"
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
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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Other property types in Kennedyville

Family-Friendly Cottage, Walk to the Beach!

10.0 out of 10, Exceptional, (18)
"Another amazing stay at Robin’s Rest. Highly recommend for a quiet weekend getaway "
Family-Friendly Cottage, Walk to the Beach!

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (75)
"EasyvPeasy place."
The price is AU$247
includes taxes & fees
28 Nov - 29 Nov
First Floor Studio Apartment in Historic Chestertown

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.8 out of 10, Exceptional, (26)
"The house is spacious (more than the photos may lead you to believe), with numerous gathering centers inside and out. My guests enjoyed the dock at sunset and the fire pit by the water. The patio under the house had a charcoal grill and ample space for tables and chairs. Though our weekend had perfect weather, the covered patio made the place "weatherproof" had it rained. There is tons of parking, and a beautiful view over the water. The Host was readily available via VRBO messaging, Usually...
Waterfront Oasis w/ Private Dock, 3BR/2BA
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.
Beautiful view of the beach with palm trees

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