Kennedyville, Maryland holiday accommodation: short-term house rentals & properties

Discover a selection of holiday rentals in Kennedyville that are perfect for your trip. Holiday rentals offer the amenities that you expect for your family, friends or furry companion, such as parking and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Find the best place to stay - Kennedyville

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Sleeps 25 · 9 bedrooms · 6+ bathrooms

Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

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

Sleeps 16 · 6 bedrooms · 5+ bathrooms

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Find the perfect holiday rental for your Kennedyville getaway

Learn about the unique charm of Kennedyville with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Kennedyville

Are you looking for things to do in the area? Venture out of your cosy holiday rental and check out everything that makes Kennedyville a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

Bulle Rock Golf Course (17.9 mi / 28.8 km)
Crow Farm and Vineyard (3.6 mi / 5.8 km)
Crumpton Auction (6.7 mi / 10.8 km)
Tilmon's Island Winery (10.2 mi / 16.4 km)
Cassinelli Winery and Vineyards (12 mi / 19.3 km)
Back Creek Golf Club (18.4 mi / 29.6 km)

Exploring the natural features in Kennedyville

Whether you're an adventurous traveller or just want to take in the scenery, Kennedyville is a great place to get outside. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

Betterton Beach (5.8 mi / 9.4 km)
Elk Neck State Park (11.9 mi / 19.2 km)
Gunpowder Falls State Park (19.4 mi / 31.2 km)
Susquehanna State Park (22.3 mi / 35.8 km)
Millard Tydings Memorial Park (16.9 mi / 27.2 km)
Garrett Island Beach (18.5 mi / 29.8 km)

Transport options to and around Kennedyville

Fly into Baltimore, MD (MTN-Martin State), the closest airport, located 22.8 mi (36.8 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Kennedyville?

The average price for a holiday home in Kennedyville can vary based on factors such as property type, length of stay and time of year. Whether you're thinking about a villa with space for extended family or an apartment that's perfect for two, just enter your dates of travel to see some great-value stays.

How much does it cost to rent a beach house in Kennedyville?

When you travel and the style and size of the property will influence how much you'll pay for your beachside escape. Enter your Kennedyville travel dates to view your available options on Stayz. Looking for basics like WiFi, or perks like a private pool? Use our filters to choose the amenities and features you want in your home.

What are the top attractions for families in Kennedyville?

Keep the kids busy at these fantastic family-friendly attractions in Kennedyville:

Historical Society of Kent County Maryland
River Arts Chestertown
Garfield Centre for the Arts at the Prince Theatre

How old do you have to be to rent a holiday home in Kennedyville?

The minimum age is normally 16, 18 or 21. It can change from one property to another on Stayz, so check the rules of your chosen Kennedyville holiday home before booking your stay.

How long can I rent a holiday home in Kennedyville for?

The amount of time you can rent a Kennedyville holiday home for is up to the property. Simply enter your dates of travel to find available options that offer extended stays. They feature the things you need to make your extended trip more enjoyable like air conditioning and kitchens. Some holiday homes may also offer discounted weekly or monthly prices, so you can stay even longer for less.