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Windsor vacation rentals

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Top-rated vacation rentals in Windsor

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile in Healdsburg includes equipped kitchen. Pick up breakfast needs before arriving. House truth: Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. It can be disruptive to sleep (or not, some say it isn't a bother). LOFT AVAILABLE BUT TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. TOT #3294N
$212 per night
Guest suite in Windsor
Private Entrance Suite in Heart of Wine Country
Situated in an upscale neighborhood, this exquisite guest suite boasts a private entrance on a safe, quiet cul-de-sac in the heart of the wine country. The en-suite is perfect for a romantic getaway, comfortable for an infant or small child, and ideal for the business traveler. We are 5 miles from Healdsburg and 3 from the Sonoma Co. Airport. Three parks within 4 miles encompass over 20 miles of hiking/biking. The Russian River, Redwoods, and Sonoma Coast are only a short, panoramic drive away.
$106 per night
Home in Windsor
Winelight Vineyard Home With Spa
Available for minimum 3 day rental. Gated driveway, private, scenic, safe, secure, and impeccably clean. Unwind, prepare dinner on granite counter tops in this newly remodeled well-stocked gourmet kitchen. Enjoy plush amenities, fine decor, hot tub, romantic fireplace, French doors leading to outdoor decks, secluded rural vibe, reliably fast internet. Close to Sonoma County's best wineries, breweries and restaurants. There is a guest laundry, designer carport, and ample parking for guests.
$239 per night

Stay near Windsor's top sights

Riverfront Regional Park34 locals recommend
Sonoma County Airport28 locals recommend
Windsor Town Green34 locals recommend
Kendall-Jackson Wine Estate & Gardens46 locals recommend
Airport Stadium 1221 locals recommend
KC's American Kitchen23 locals recommend

Other great vacation rentals in Windsor

Home in Windsor
Home near golf course w/Hot tub in Windsor
$346 per night
Cottage in Windsor
Vineyard Cozy Cottage & Hot Tub
$213 per night
Loft in Windsor
The Loft Under The Oaks
$133 per night
Home in Healdsburg
Wine Country Cottage Walkable to River or Downtown
$223 per night
Guesthouse in Santa Rosa
The Urban Oasis with extended outdoor living
$110 per night
Guest suite in Santa Rosa
Dedicated Patio, Roku & Self Check-In
$98 per night
Guesthouse in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
$180 per night
Guesthouse in Healdsburg
Healdsburg Cottage-Workspace, Walk to Plaza
$200 per night
Apartment in Santa Rosa
Private Getaway in West Santa Rosa
$95 per night
Guest suite in Santa Rosa
Private upstairs guest suite with queen bed
$92 per night
Guest suite in Healdsburg
Bunkhouse at Side Road Farm
$220 per night
Guesthouse in Santa Rosa
Sonoma County Vineyard Tank House w/ Fast WiFi
$210 per night

Quick stats about vacation rentals in Windsor

Total rentals

310 properties

Rentals with dedicated workspaces

150 properties have a dedicated workspace

Rentals with a pool

190 properties have a pool

Pet-friendly rentals

60 properties allow pets

Family-friendly rentals

220 properties are a good fit for families

Total number of reviews

11K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Windsor