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Search results; Over 1,000 homes in Windsor

Top guest favourite
Cabin in Windsor
Middle Lake Retreat *with hot tub*
2 bedrooms, 4 beds, 1 private bathroom
30 Aug – 4 Sept
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4.99 out of 5 average rating, 151 reviews
Top guest favourite
Serviced apartment in Windsor
New Studio Suite in Historic Gem
4.9 out of 5 average rating, 72 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Top guest favourite
Guest suite in Windsor
Dar's Dwelling - A suite place to stay.
4.93 out of 5 average rating, 189 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Flat in Windsor
Quiet Country 2 Bedroom Suite
5.0 out of 5 average rating, 97 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Sept – 4 Oct
Superhost
Home in Windsor
The Martock House · Ski-Inspired Sauna Retreat
4.84 out of 5 average rating, 45 reviews, 2 bedrooms, 4 beds, 1 bathroom
23–28 Aug
Top guest favourite
Apartment in Windsor
Quiet Downtown Apartment with Everything You Need
4.96 out of 5 average rating, 117 reviews, 1 bedroom, 1 bed, 1 bathroom
29 Aug – 3 Sept
Guest favourite
Flat in Windsor
Minutes to Wine Country- The Sunshine Suite
4.96 out of 5 average rating, 93 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Chalet in Windsor
Rocky Brook Chalet
4.96 out of 5 average rating, 260 reviews, 4 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
Guest favourite
Flat in Windsor
Renovated Studio Apartment, full amenities
4.9 out of 5 average rating, 90 reviews, 1 bed, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Cottage in Windsor
Wildberry Cottage
4.98 out of 5 average rating, 64 reviews, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Home in Windsor
Mounce Mansion - Country House-Sleeps 12+
4.98 out of 5 average rating, 97 reviews, 5 bedrooms, 7 beds, 2.5 bathrooms
14–19 Sept
Guest favourite
Cabin in Windsor
Private cabin on a lake - kayaks, SUP, fire pit
4.97 out of 5 average rating, 211 reviews, 3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Cottage in Windsor
Falls Lake Cottage Retreat
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 5 beds, 2 bathrooms
26–31 Oct
Guest favourite
Guest suite in Windsor
Cozy Suite with Private Entrance
4.84 out of 5 average rating, 120 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Sept
Top guest favourite
Cottage in Windsor
Knotty Pine Cottage - cozy lakeside getaway!
4.93 out of 5 average rating, 381 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
Guest favourite
Cabin in Windsor
All Decked Out
4.96 out of 5 average rating, 71 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
Top guest favourite
Flat in Hantsport
Historic East Coast Apartment *Private Sauna*
5.0 out of 5 average rating, 174 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Oct
Home in Windsor
Hemlock Hill Cottage
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Windsor
Gateway to Annapolis Valley | Windsor Studio Suite
4.88 out of 5 average rating, 16 reviews, 1 bed, 1 bathroom
15–20 Aug