Holiday Rentals in Kennedyville

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Holiday Rentals in Kennedyville

Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

2.0 star property
8.8 out of 10, Excellent, (3)
"Would I stay here again? No. Would I recommend it to a friend? Also no.While the unit was clean, it felt quite tired and in need of a refresh. The kitchen was minimally equipped, with very few pots and pans, making it difficult to cook meals. Additionally, there were air fresheners and purifiers in every room, which made us wonder if they were masking an underlying issue. Overall, the space could benefit from some updates and better preparation for guests."
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (99)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is €151
includes taxes & fees
25 Sept - 26 Sept
First Floor Studio Apartment in Historic Chestertown

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (170)
"Easy check in process. House very clean. Going location. "
Chesapeake Bay House with Dock & Private Beach

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

9.4 out of 10, Exceptional, (35)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (13)
"Always a nice get away…."
The price is €245
includes taxes & fees
30 Aug - 31 Aug
Historic Chesapeake City Stay

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (142)
"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 €538
includes taxes & fees
1 Sept - 2 Sept
5-bedroom vacation home 5 minutes from historic Charlestown

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

9.2 out of 10, Wonderful, (5)
The price is €278
includes taxes & fees
1 Sept - 2 Sept
Charming 2-bedroom cabin close to Fair Hill on horse farm

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (52)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay

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

9.6 out of 10, Exceptional, (61)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

10.0 out of 10, Exceptional, (10)
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (46)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is €267
includes taxes & fees
1 Sept - 2 Sept
BAYSIDE BUNGALOW

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

10.0 out of 10, Exceptional, (20)
"Very nice cottage, as advertised"
The price is €200
includes taxes & fees
28 Sept - 29 Sept
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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

10.0 out of 10, Exceptional, (12)
"A very well maintained and comfy apartment that is just a short walk to the heart of Rock Hall. My family especially enjoyed the large private backyard. Rick made sure we had everything we needed."
The price is €261
includes taxes & fees
1 Sept - 2 Sept
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (25)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.

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

10.0 out of 10, Exceptional, (8)
"Can’t say enough about how nice this place is. We had quick friendly responses from owners. Very clean and the water front view was excellent. Highly recommended "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

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

10.0 out of 10, Exceptional, (6)
"The property is everything it claims to be & more. Awesome location on the bay. Great accommodations. So peaceful. We had a wonderful time. Would highly recommend! "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

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

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
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

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 €151 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.