A calm lake surrounded by autumn-colored trees reflecting in the water.

Pleasantville houses

We found 82 houses — enter your dates for availability

Explore Pleasantville house rentals

Image of Historic former Speakeasy 4 Bdrm, walk to train and town: Pleasantville

Historic former Speakeasy 4 Bdrm, walk to train and town: Pleasantville

Sleeps 10 · 4 bedrooms · 3+ bathrooms

Image of Cozy house on the Hudson

Premier Host

Cozy house on the Hudson

Sleeps 2 · 1 bedroom · 1 bathroom

Image of Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Sleeps 13 · 5 bedrooms · 4+ bathrooms

Image of Summer fun on the river. Swim, fish, kayak and bird watch at Croton River Gorge.

Premier Host

Summer fun on the river. Swim, fish, kayak and bird watch at Croton River Gorge.

Sleeps 4 · 1 bedroom · 1+ bathroom

Image of 2BDRM COTTAGE IN PLEASANTVILLE

2BDRM COTTAGE IN PLEASANTVILLE

Sleeps 2 · 2 bedrooms · 1+ bathroom

Image of Spacious 3BR Home / Free Parking / Perfect for Families & Groups

Spacious 3BR Home / Free Parking / Perfect for Families & Groups

Sleeps 16 · 3 bedrooms · 2 bathrooms

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