A green agricultural field with rows of crops and greenhouses in the distance under a cloudy sky.

Chester villa rentals

We found 7 villa rentals — enter your dates for availability

Explore Chester villa rentals

Image of Serene 10BR Retreat w/Pool, Gym & Hot Tub

Serene 10BR Retreat w/Pool, Gym & Hot Tub

Sleeps 25 · 10 bedrooms · 4+ bathrooms

Image of Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Premier Host

Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Sleeps 16 · 7 bedrooms · 5 bathrooms

Image of 11BR Retreat w Pool, Hot Tub, Sauna & Game Room

11BR Retreat w Pool, Hot Tub, Sauna & Game Room

Sleeps 28 · 11 bedrooms · 4 bathrooms

Image of 7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Sleeps 19 · 7 bedrooms · 4 bathrooms

Image of Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC

Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC

Sleeps 25 · 8 bedrooms · 5 bathrooms

Image of Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

Sleeps 12 · 5 bedrooms · 4 bathrooms

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