A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

Bennington cottage rentals

We found 40 cottage rentals — enter your dates for availability

Explore Bennington cottage rentals

Image of Perfect for a peaceful get away in clean fresh Vermont air!

Premier Host

Perfect for a peaceful get away in clean fresh Vermont air!

4 bedrooms · 1.5 bathrooms

Image of Lake life at Woodford Cottage

Lake life at Woodford Cottage

Sleeps 6 · 2 bedrooms · 1 bathroom

Image of Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Sleeps 5 · 3 bedrooms · 1 bathroom

Image of Brookside cottage near the mountains and outdoor recreation

Premier Host

Brookside cottage near the mountains and outdoor recreation

Sleeps 4 · 2 bedrooms · 1 bathroom

Image of Bright 3-Bedroom Historical Cottage w/ pool table

Bright 3-Bedroom Historical Cottage w/ pool table

Sleeps 8 · 3 bedrooms · 2 bathrooms

Image of Private, Contemporary Home with a View of Mount Snow.

Premier Host

Private, Contemporary Home with a View of Mount Snow.

Sleeps 7 · 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