A row of houses with a mountain in the background.

Pleasant Valley houses

We found 100 houses — enter your dates for availability

Explore Pleasant Valley house rentals

Image of Peaceful getaway for outdoor enthusiasts-a modern home with a country/farm feel.

Peaceful getaway for outdoor enthusiasts-a modern home with a country/farm feel.

Sleeps 8 · 3 bedrooms · 2+ bathrooms

Image of Private Hudson Valley Home Near Wine Trail / Antiquing / Orchards

Private Hudson Valley Home Near Wine Trail / Antiquing / Orchards

Sleeps 4 · 3 bedrooms · 2 bathrooms

Image of Relaxing Lodge Retreat

Relaxing Lodge Retreat

Sleeps 14 · 6 bedrooms · 3+ bathrooms

Image of Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook

Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook

Sleeps 6 · 3 bedrooms · 2+ bathrooms

Image of Modern Getaway Retreat House on 2 Acres

Modern Getaway Retreat House on 2 Acres

Sleeps 8 · 3 bedrooms · 3 bathrooms

Image of Wappinger Cottage - Scandinavian retreat on a creek

Premier Host

Wappinger Cottage - Scandinavian retreat on a creek

Sleeps 6 · 3 bedrooms · 2 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