A boat docked at a pier during twilight with a city skyline in the background.

Photo by Patricia Knorr

Chester houses

We found 193 houses — enter your dates for availability

Explore Chester house rentals

Image of Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Premier Host

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Sleeps 8 · 4 bedrooms · 2 bathrooms

Image of Room for an Island getaway

Room for an Island getaway

Sleeps 2 · 1 bedroom · 1 bathroom

Image of Island Blue Getaway! Charming family friendly Home on Kent Island MD

Premier Host

Island Blue Getaway! Charming family friendly Home on Kent Island MD

Sleeps 8 · 3 bedrooms · 2+ bathrooms

Image of Crab Alley | Waterfront Home + Hot Tub + Game Room

Crab Alley | Waterfront Home + Hot Tub + Game Room

Sleeps 10 · 4 bedrooms · 2 bathrooms

Image of Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails

Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails

Sleeps 9 · 4 bedrooms · 2+ bathrooms

Image of Charming Waterfront home, Kent Island, Maryland!

Charming Waterfront home, Kent Island, Maryland!

Sleeps 8 · 4 bedrooms · 3 bathrooms

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value