A vineyard with rows of grapevines and a pond.

Keswick cottages

We found 88 cottages — enter your dates for availability

Explore Keswick cottage rentals

Image of Charming Cottage on beautiful Farm & Vineyard

Charming Cottage on beautiful Farm & Vineyard

Sleeps 4 · 2 bedrooms · 1+ bathroom

Image of Stonemont Farm Cottage with Hot Tub! in Keswick near Vineyards

Premier Host

Stonemont Farm Cottage with Hot Tub! in Keswick near Vineyards

Sleeps 10 · 3 bedrooms · 2 bathrooms

Image of Loveshack, a charming tiny house on a 5 acre farm

Loveshack, a charming tiny house on a 5 acre farm

Sleeps 4 · 1 bedroom · 1 bathroom

Image of Cowboy hide-a-way cottage with hot tub on historic farm close to everything

Premier Host

Cowboy hide-a-way cottage with hot tub on historic farm close to everything

Sleeps 4 · 2 bedrooms · 1 bathroom

Image of Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

Sleeps 7 · 2 bedrooms · 1 bathroom

Image of The Guest Cottages at La Fourche

The Guest Cottages at La Fourche

Sleeps 10 · 3 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