Windsor Rentals

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113 Houses

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Responds fast! avg. 1 hour 31 minutes

Price per night from

$243

Responds fast! avg. 1 hour 31 minutes

Price per night from

$193

Superbowl 50; February 3-10

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$571

Responds fast! avg. 1 hour 31 minutes

Price per night from

$182

Sonoma Wine Nest - Location! Location! Location!

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$371

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

$646

Great rentals within 20 miles that match your search

Spacious Studio in Sonoma wine country

Santa Rosa studio

  • Studio
  • 1 bathroom
  • sleeps 3

Price per night from

$217

Urban Retreat in the Heart of St. Helena

St. Helena house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$286

Lovely Country Cottage in Heart of Wine Country

Petaluma cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$172

Deja Blu-Magical Ocean Front Property (Beach View)

Bodega Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$907

Cabin Compound on the Creek in the Redwoods

Cazadero log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$132

"Royal Pacific" Luxury Ocean And Golf Course Home

Bodega Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$1,084

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

$1,820

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

$6,845

The Stone Lodge in Kenwood ~ 5 bedroom/5 bath

Kenwood house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$3,993

Kenya's Kastle

Healdsburg house

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 8

Price per night from

$209

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

Kenwood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$383

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

Santa Rosa house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$477

Villa LaFleur Sonoma

Kenwood villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$1,997

Healdsburg Downtown Cottage

Healdsburg cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$286

Heiter House - the perfect getaway in Wine Country

Kenwood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$429

Price per night from

$742

Wine Country Redwood Estate

Santa Rosa villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 15

Price per night from

$1,592

Alexander Valley Lodge on 54 acres with Pool and Hot Tub

Geyserville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$1,027

Grand Riverfront Estate with Dock, Minutes from the Beach

Monte Rio house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$257

Spacious 5-bedroom home: hot tub, pool table, spectacular views

Bodega Bay house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

Price per night from

$713

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

$514

WALK to Wineries from this Gorgeous Designer Home!

Kenwood house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$565

Stunning Mid-Century Modern Retreat

Guerneville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$314

Luxury secluded redwood retreat in Green Valley

Forestville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$229

The Cottage

Santa Rosa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$341

Price per night from

$508

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

Santa Rosa house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,369

Wine Country apartment

Larkfield-Wikiup house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$343

Modern 2BR Condo at The Meadows at Fountaingrove

Fulton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 15 minutes

Price per night from

$237

Price per night from

$679

Viewing 38 of 113
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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