
House holiday rentals in Windsor
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Top-rated house rentals in Windsor
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor house rentals
House rentals with a pool

Luxury home, hot tub/spa pool, walk to restaurants

Vineyard Vista, Modern Farmhouse Cottage with Pool

20 Acre Ranch w/Vineyards, Pool, Hot Tub, & Views!

*Heated* Swimming Pool Retreat Near Sonoma Square

Luxury home (+ pool house) with views, pool & spa

Hot Tub/Pool ~ Walk To Wine, Shops & Restaurants

Lovely and Spacious Ranch-Style Home With a Poolside Oasis

4/3 Vineyard Home With Pool & Views (Sleeps 8)
Weekly house rentals

Family Friendly Charming 2 BD

Healdsburg 2br Cottage with Private Yard!

Vineyard Retreat | 3BR Home Near Sonoma & Napa

Charming Windsor Home

The Ranchette- luxe 1 BR w/hot tub/ & prvt. patio

Forever Sunday: Walk to Town | Redwoods | Firepit

KH: Life is a Beach-DOG Friendly

Wine Country Escape with 4 King beds & hot tub!
Private house rentals

Green Valley, Sonoma County at a Working Winery.

Thornsberry House, A Luxe Wine Country Getaway

Casa Del Sol, Secluded with Views

Annadel House Retreat- Stunning Wine Country Luxe!

Large Charming Home Surrounded by a Vineyard

The Deer Retreat – Privacy and Comfort

Riverside Lodge House in Guerneville

Wine Country Fairgrounds AC BBQ Downtown Stocked!
Quick stats about house rentals in Windsor
Total rentals
90 properties
Total number of reviews
5.6K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Destinations to explore
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- Rentals with a fireplace Windsor
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- Clam Beach
- Sonoma Coast State Park
- Muir Woods National Monument
- Point Reyes National Seashore
- Dominus Estate
- Chandon
- Six Flags Discovery Kingdom
- Caymus Vineyards
- Pebble Beach
- Safari West
- Santa Maria Beach
- Gleason Beach
- South Beach
- Schoolhouse Beach
- North Salmon Creek Beach
- Point Reyes Beach
- Doran Beach
- Portuguese Beach
- Chateau St. Jean
- Black Point Beach
- Shell Beach
- Kistler Vineyards-Trenton Roadhouse Tastings by Appointment
- Driftwood Beach
- Kelham Beach