Windsor Rentals

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Responds fast! avg. 1 hour 45 minutes

Price per night from

$243

Responds fast! avg. 1 hour 45 minutes

Price per night from

$193

Superbowl 50; February 3-10

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$573

Responds fast! avg. 1 hour 45 minutes

Price per night from

$182

Sonoma Wine Nest - Location! Location! Location!

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$373

Chalk Hill Cottage - 1 BR w/ Sleeper Sofa

Windsor cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$172

Tranquil vineyard retreat

Windsor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$189

With Pool & Hot Tub, Beautifully Appointed 4BR Home!

Windsor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$588

Great rentals within 20 miles that match your search

Deja Blu-Magical Ocean Front Property (Beach View)

Bodega Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$911

Cabin Compound on the Creek in the Redwoods

Cazadero log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$132

Spa, Bocce, Bbq Kitchen, Walk or Bike to Wineries

Kenwood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$384

Downtown B&B close to Arts, Food, Wine great beer

Santa Rosa house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$479

Spacious Studio in Sonoma wine country

Santa Rosa studio

  • Studio
  • 1 bathroom
  • sleeps 3

Price per night from

$218

Urban Retreat in the Heart of St. Helena

St. Helena house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$287

Lovely Country Cottage in Heart of Wine Country

Petaluma cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$172

"Royal Pacific" Luxury Ocean And Golf Course Home

Bodega Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$1,089

Enchanted Forest Estate

Guerneville house

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 28

“Best place to stay with a large group” We had the best time staying at the two side-by-side houses in Russian river. We have 6 families and way too many kids =) The layout and set up of the houses was perfect. The downstairs play rooms for the kids was ideal. The park-like backyard and easy access to the river made this place one of the best we have ever stayed at. In addition, they have everything you could ever need during your stay from the Bbq's, well stocked kitchens to the canoe and kayak's. We will definitely come back.

Price per night from

$1,828

The Ranch Above St Helena ~ 5 bedroom 8 1/2 bath Overlooking St. Helena

St. Helena house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 12

Price per night from

$6,874

The Stone Lodge in Kenwood ~ 5 bedroom/5 bath

Kenwood house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$4,010

Kenya's Kastle

Healdsburg house

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 8

Price per night from

$210

Price per night from

$745

Villa LaFleur Sonoma

Kenwood villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$2,005

Healdsburg Downtown Cottage

Healdsburg cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$287

Heiter House - the perfect getaway in Wine Country

Kenwood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$431

Bohemian Creekside Cottage minutes from Occidental and Sebastopol

Occidental house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$343

Alexander Valley Lodge on 54 acres with Pool and Hot Tub

Geyserville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$1,031

Beautiful Forest Villa Retreat in Sonoma County

Cazadero villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

Price per night from

$1,375

Grand Riverfront Estate with Dock, Minutes from the Beach

Monte Rio house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$258

Wine Country Getaway in Napa/Sonoma, Hot Tub, Redwoods and Creek Views

Santa Rosa house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$516

Stunning Mid-Century Modern Retreat

Guerneville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$315

Luxury secluded redwood retreat in Green Valley

Forestville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$230

The Cottage

Santa Rosa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$343

The TreeHouse- Charming Cabin in the Redwoods

Monte Rio house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$189

Wine Country apartment

Larkfield-Wikiup house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$344

Price per night from

$510

Wine Country Luxury Home-Pool, Hot Tub, Brush Creek

Santa Rosa house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,375

Price per night from

$567

Modern 2BR Condo at The Meadows at Fountaingrove

Fulton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$238

Viewing 38 of 114
rentals in Windsor

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About Windsor

Situated within Sonoma County on California's North Coast, Windsor is a historic town dating back to the 1870s and part of the state's renowned wine country region. Today, people come from all over the globe to experience the area's exquisite natural beauty, culinary delights, outdoor activities, and of course, the unique and award-winning vineyards nearby. There are plenty of casual and fine dining restaurants to be discovered, as well as various cultural activities to enjoy downtown and within the city's parks and playgrounds. Shopping excursions for antiques, clothing, jewelry, and crafts are easy to find. Visitors will also encounter a cornucopia of fruits, vegetables, and homegrown goodies at the Windsor Farmers Market, which runs all year long.

Here are some of the town highlights you'll want to take include in your itinerary:

  • Old Downtown Windsor: This historic hub of the city is full of shops, restaurants, and cafes.
  • Windsor Town Green: As the central spot for fun family activities, this space features plenty of room for play, picnics, outdoor concerts and more.
  • Russian Hill Estate Vineyards and/or Martinelli Vineyards: These two wineries offer tastings and tours in beautiful countryside surroundings.
  • Ballooning: A hot-air balloon experience offers truly breathtaking sights of Sonoma County Wine Country.
  • The Windsor Golf Club: This former PGA tournament stop provides a challenging course in a picturesque setting.
  • Powell's Sweet Shoppe: As an old-fashioned candy store, this is the sweet spot for adults and kids alike.

After a long day of exploring all that Windsor has to offer, you can settle into your vacation rental, whether it be an apartment or condo downtown or a villa with spectacular vineyard views.

Temperatures are mild year-round, but harvest time, around September and October, is the ideal season to see all the sights. There are also several annual events that are attractive to travelers including Taste Alexander Valley in May, a food and wine event, and Summer Nights on the Green, movie showings under the stars during June, July, and August.

To continue your journey in the wine country, you can visit additional nearby attractions in Santa Rosa and Sonoma. If you are craving some big city adventure, San Francisco, is located about an hour south of Windsor.

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