Vacation rentals in Windsor

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windsor

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

Guest favourite
Guesthouse in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N
Jul. 23 – 30
$297 CAD per night
4.98 out of 5 average rating, 246 reviews
Guest favourite
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.
Aug. 12 – 19
$202 CAD per night
4.98 out of 5 average rating, 353 reviews
Guest favourite
Home in Windsor
Gorgeous Victorian in the HEART of Windsor
Gorgeous renovated Queen Anne Victorian located in the heart of Windsor, CA combines quality finishes, modern convenience & vintage details. With a stylish kitchen, high ceilings, 3 beds/2 baths on a single level, HVAC & a huge lot with a Bocce Court. Walking distance to the Town Green, restaurants, wine tasting rooms and shopping. Just 3.5 miles from the Sonoma County Airport (STS), 5 miles to downtown Healdsburg, in the heart of the Russian River Valley & just 57 miles from the Golden Gate.
May 7 – 14
$702 CAD per night
4.99 out of 5 average rating, 101 reviews

Popular amenities for Windsor vacation rentals

Stay near Windsor's top sights

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

Other great vacation rentals in Windsor

Guest favourite
Guest suite in Santa Rosa
Private upstairs guest suite with queen bed
Feb. 17 – 24
$169 CAD per night
4.97 out of 5 average rating, 143 reviews
Guest favourite
Guesthouse in Sebastopol
Sun Drenched Flat
Jun. 23 – 30
$215 CAD per night
4.93 out of 5 average rating, 674 reviews
Guest favourite
Guest suite in Graton
The Flying Pig
May 16 – 23
$163 CAD per night
4.95 out of 5 average rating, 261 reviews
Guest favourite
Home in Windsor
Luxurious home and pool
Apr. 19 – 26
$894 CAD per night
4.93 out of 5 average rating, 147 reviews
Superhost
Villa in Healdsburg
Hilltop Vista Villa
Nov. 25 – Dec. 2
$705 CAD per night
4.94 out of 5 average rating, 108 reviews
Guest favourite
Apartment in Santa Rosa
Robin's Nest
Dec. 23 – 30
$178 CAD per night
4.99 out of 5 average rating, 251 reviews
Guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
Nov. 13 – 20
$466 CAD per night
4.97 out of 5 average rating, 467 reviews
Guest favourite
Guesthouse in Sebastopol
Modern Bungalow Downtown Sebastopol
Sep. 7 – 14
$190 CAD per night
4.98 out of 5 average rating, 427 reviews
Superhost
Home in Santa Rosa
Charming 1-Bd Granny Unit Amid Wineries
Jan. 5 – 12
$246 CAD per night
4.92 out of 5 average rating, 203 reviews
Guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
Nov. 24 – Dec. 1
$302 CAD per night
4.96 out of 5 average rating, 428 reviews
Guest favourite
Apartment in Windsor
Windsor 2 Bed/2 Bath Condo ~Pool~Hot Tub~Gym
Dec. 28 – Jan. 4
$324 CAD per night
4.88 out of 5 average rating, 146 reviews
Guest favourite
Condo in Santa Rosa
Cozy One Bedroom Townhouse
May 6 – 13
$139 CAD per night
4.92 out of 5 average rating, 60 reviews

Quick stats about vacation rentals in Windsor

Total rentals

350 properties

Rentals with dedicated workspaces

160 properties have a dedicated workspace

Rentals with a pool

230 properties have a pool

Pet-friendly rentals

60 properties allow pets

Family-friendly rentals

250 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