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 house rentals in Windsor
House rentals with a pool
Home in Santa Rosa
4.98 out of 5 average rating, 101 reviewsPacific Gardens Retreat
30 Jan – 6 Feb
Home in Occidental
4.96 out of 5 average rating, 115 reviewsModern mid-century-inspired, Deer Ranch
18–25 Dec
Home in Santa Rosa
4.98 out of 5 average rating, 164 reviewsHappy House w/large pool, hot tub & chefs kitchen
28 Nov – 5 Dec
Home in Glen Ellen
5.0 out of 5 average rating, 127 reviewsTuscan Wine Country Villa with Pool sleeps 6
7–14 Jan
Home in Kenwood
4.99 out of 5 average rating, 271 reviewsSonoma Vineyard Home With Pool & Stunning Views
21–28 Mar
Home in Sebastopol
4.98 out of 5 average rating, 150 reviewsSebastopol Gem, The Birdhouse. Hottub. Pool. Views
6–13 Mar
Home in Santa Rosa
4.87 out of 5 average rating, 164 reviewsHot Tub/Heated Pool ~ Walk To Shops & Restaurants
29 Jul – 5 Aug
Home in Santa Rosa
4.9 out of 5 average rating, 109 reviewsSonoma County Oasis with Heated Pool
8–15 Jan
Weekly house rentals
Home in Healdsburg
4.98 out of 5 average rating, 398 reviewsVineyard Modern Barn House - Dry Creek Valley
24–31 Aug
Home in Santa Rosa
5.0 out of 5 average rating, 125 reviewsModern Wine Country Home /Game Room/Near New Park
18–25 Oct
Home in Occidental
4.99 out of 5 average rating, 114 reviewsGuest favorite: Serene retreat on private road
7–14 Jun
Home in Santa Rosa
4.96 out of 5 average rating, 191 reviewsGET Away to WINE Country- 3 bdrm Home
23–30 Sep
Home in Healdsburg
4.89 out of 5 average rating, 297 reviewsPeaceful location, hot tub, fire pit, game room!
13–20 Mar
Home in Healdsburg
4.88 out of 5 average rating, 138 reviewsModern Home in Hburg Wine Country
11–18 Nov
Home in Healdsburg
4.91 out of 5 average rating, 127 reviewsDry Creek w/Hot Tub, Bocce, Vineyard Views
29 Mar – 5 Apr
Home in Santa Rosa
4.94 out of 5 average rating, 127 reviewsWest End Neighborhood Cottage
28 Jun – 5 Jul
Private house rentals
Home in Forestville
4.96 out of 5 average rating, 242 reviewsForest Cozy Home
25 Nov – 2 Dec
Home in Santa Rosa
4.92 out of 5 average rating, 205 reviewsCharming 1-Bd Boho Flat Amid Wineries
25 Aug – 1 Sep
Home in Santa Rosa
4.84 out of 5 average rating, 168 reviewsModern " Vineyards Found" Wine Country Home
20–27 Dec
Home in Santa Rosa
4.97 out of 5 average rating, 150 reviewsAMITABHA Wine Country Cottage
18–25 Apr
Home in Healdsburg
5.0 out of 5 average rating, 60 reviews10 Acre Vineyard Cottage w/Hot Tub + Bocce Court
9–16 Apr
Home in Windsor
5.0 out of 5 average rating, 40 reviewsVino Velo House - Vineyards & Restaurants Nearby
16–23 Sep
Home in Windsor
4.86 out of 5 average rating, 58 reviewsEscape to Golf & Wine in the Heart of Wine Country
24 Sep – 1 Oct
Home in Healdsburg
5.0 out of 5 average rating, 9 reviewsThe Dragonfly Healdsburg
26 Feb – 5 Mar
Quick stats about house rentals in Windsor
Total rentals
110 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
5.9K reviews
Destinations to explore
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