Four unique stays. One walkable downtown.
Make yourself at home in Windsor.
Your home base for the Annapolis Valley.
Explore our staysFour stays. Find yours.
From a cozy studio for two to a three-bedroom home for the whole family, each one a short walk from Windsor’s cafés, shops and waterfront.
New 
The Main Street Suite
A bright one-bedroom right on Windsor’s main street.
- Sleeps 2
- 1 bedroom
- 1 bath
Guest favourite 
The Valley Studio
A modern studio and the gateway to the Annapolis Valley.
- Sleeps 2
- Studio
- 1 bath
- 4.85 (46)
Guest favourite 
The Loft
A newly renovated top-floor suite with town views.
- Sleeps 2
- 1 bedroom
- 1 bath
- 4.85 (20)
New 
The Gerrish House
A whole three-bedroom home for family and friends.
- Sleeps 7
- 3 bedrooms
- 2 baths
On Gerrish Street
Small-town charm, right outside your door.
Every stay sits on Gerrish Street, in the heart of downtown Windsor. Park once and walk to coffee in the morning, local shops in the afternoon and dinner at night.
Inside, you’ll find freshly renovated spaces with full kitchens, fast wifi and self check-in, so you can arrive on your own schedule and settle straight in.
Find your stay
Aunt Lisa’s, a summer favourite on Gerrish Street.
Explore Windsor
The gateway to the Annapolis Valley.
Windsor puts the best of the Valley within easy reach: wineries, ski hills, the world’s highest tides and the city of Halifax.
- On foot Downtown WindsorCafés, shops and the waterfront
- 7 min Bent Ridge WineryValley wine, minutes from town
- 11 min Ski MartockSkiing and snow tubing in winter
- 15 min Avondale Sky WineryA winery in a restored church
- 30 min WolfvilleWineries, restaurants, Acadia University
- 40 min Burntcoat HeadThe world’s highest tides
- 45 min Downtown HalifaxAn easy day trip to the city
Hosted by Dan
Average guest rating out of 5
Nine years as an Airbnb Superhost, with guest favourites on Gerrish Street.
