Kennedyville Holiday Rentals

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Holiday Rentals 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!
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
10.0 out of 10, Exceptional, (73)
"A hidden gem! Beautiful location on the bay with the cutest town!!! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (71)
"Just what we needed for the night! Thank you "
The price is AU$226
includes taxes & fees
9 Oct - 10 Oct
First Floor Studio Apartment in Historic Chestertown
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (29)
"What a great location, practically on the water! Betty Ann was very responsive and everything about this place was easy!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (43)
"We really enjoyed the water views & walking by the water. It was a very enjoyable and relaxing stay."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (29)
"Ideal vacation for family of 22. It suited everyone."
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (52)
"Nice. Close to downtown. Great backyatd"
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
10.0 out of 10, Exceptional, (45)
"We had a wonderful stay at Nauti or Knot. The property was beautiful, spacious, clean and as described. The amenities were plentiful and thoughtful. Diane was easy to reach with any questions. We would love to stay here again! Five stars!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
9.4 out of 10, Exceptional, (32)
"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
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 Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, (23)
"Clean with comfortable beds!"
Waterfront Oasis w/ Private Dock, 3BR/2BA
Beautiful, spacious, quiet waterfront house!
10.0 out of 10, Exceptional, (42)
"Awesome spot for two young families (4A, 3K). Easy drive to local stores and restaurants. Plenty to do right at the house. Fantastic sunrise view from the back deck. Hot tub and ping pong 🏓 were a blast for our kids! "
Beautiful, spacious, quiet waterfront house!
Chesapeake City Quiet Overlook
10.0 out of 10, Exceptional, (11)
"My wife and I booked Jane’s house for our wedding weekend in Chesapeake city. Jane allowed us to use her property for our wedding of 40 ppl. She could not have been nicer or more accommodating for this special occasion. She responded to all of our questions quickly and even made special offers to make our wedding weekend even more special. I cannot say enough nice things about Jane. The house and property were gorgeous in a really great location along the canal in Chesapeake city. The views...
Chesapeake City Quiet Overlook
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.4 out of 10, Exceptional, (19)
"Everything would have been wonderful except for the attitude of the owner who was quick to blame us for something we had no control of. We were quite content and lucky the bath house was so convenient because one of the toilets on the boat did not work. He insisted it was our fault and was quick to blame. In his defense he did send someone out very quickly to see if it could be fixed. "
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Amazing Waterfront Home on the Bush River
10.0 out of 10, Exceptional, (17)
"We stayed here for our wedding weekend leading up to the big day with our families and this couldn't have asked for a better location and place to relax."
Amazing Waterfront Home on the Bush River
Captivating Chesapeake experience
10.0 out of 10, Exceptional, (249)
"We had a wonderful stay at this beautiful property. The water views are amazing and it was so relaxing! The house was very clean and well maintained. Everything we expected it to be from the listing, actually more charming and comfortable than the pictures show. Thank you. "
Captivating Chesapeake experience
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (29)
"Sweet cozy cottage with all the amenities and comforts of home. Wine was waiting for us, with coffee, robes, and more! You don’t need to bring a thing!"
The price is AU$401
includes taxes & fees
10 Oct - 11 Oct
BAYSIDE BUNGALOW
Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is AU$437
includes taxes & fees
11 Oct - 12 Oct
Historic Chesapeake City Stay
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
Top of the Chesapeake - Minutes from Historic Charlestown
9.8 out of 10, Exceptional, (133)
""Oh, down in Chesapeake Catching rock around fishing creek The soft-shell crabs play hide and seek Down in Chesapeake." We LOVE the Chesapeake area and have stayed up and down the bay, mostly midway and lower. This area on the upper bay is so close to Philadelphia and, although there are tourists around like us, it doesn't feel touristy unless you go into North East, downtown (which is still worth eating a meal or getting ice cream in that cute little town)! Our stay felt private, and we had...
The price is AU$972
includes taxes & fees
7 Oct - 8 Oct
Top of the Chesapeake - Minutes from Historic Charlestown
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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 types of properties in Kennedyville you may be interested in

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!
Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 star property
7.2 out of 10, Good, (1007)
"My stay was great! Just disappointed that all amenities are down! Pool,laundry,gym and business center are all closed!!!! "
The price is AU$88
includes taxes & fees
16 Oct - 17 Oct
Quality Inn & Suites Bel Air I-95 Exit 77A
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
2.5 star property
8.2 out of 10, Very good, (1003)
"Ok for older hotel"
The price is AU$103
includes taxes & fees
9 Oct - 10 Oct
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
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.

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?

Captivating Chesapeake experience: This holiday home rental outside of Kennedyville is located on the waterfront, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

What’s there to see and do in Kennedyville?

While exploring the area, visit family-friendly sights like Havre de Grace Maritime Museum, or get outside and enjoy nature at Betterton Beach. Crow Farm and Vineyard and Washington College are a couple of places you'll find in the wider area.

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.