Windsor cottage rentals

We found 54 cottage rentals — enter your dates for availability

Where to?

Dates

May 2026

June 2026

Explore Windsor cottage rentals

Premier Host

Sleeps 4 · 1 bedroom · 1 bathroom

Sleeps 4 · 1 bedroom · 1+ bathroom

Premier Host

Sleeps 2 · 1 bedroom · 1 bathroom

Premier Host

Sleeps 2 · 1 bathroom

We enjoyed Carol’s lovely cottage, a welcoming oasis

Anne U.

Stayed Nov 2023

Very nice place. It has all the comforts of home. Will absolutely stay here again. Great for that Wine Country getaway.

Charlotte L.

Stayed Jan 2020

House

Condo/Apartment

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