Windsor Rentals

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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

$573

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

$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

$190

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

Wine Country Redwood Estate

Santa Rosa villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 15

Price per night from

$1,601

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

$1,033

Grand Riverfront Estate with Dock, Minutes from the Beach

Monte Rio house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$259

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

$517

The Cottage

Santa Rosa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$343

Stunning Mid-Century Modern Retreat

Guerneville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$316

Luxury secluded redwood retreat in Green Valley

Forestville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$230

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

Santa Rosa house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,377

Wine Country apartment

Larkfield-Wikiup house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$345

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

$238

Price per night from

$567

Price per night from

$510

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

Bodega Bay house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

Price per night from

$716

A Perfect Getaway in The Wine Country

Santa Rosa house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$366

Price per night from

$3,434

The Spectacular Spyglass Treehouse

Occidental tree house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 38 minutes

Price per night from

$636

Warm & Welcoming Family Retreat in Wine Country

Santa Rosa house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$690

Centrally Located! Spacious Modern 3BR w/ Parking

Santa Rosa house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Price per night from

$197

Peaceful Modern Sta Rosa Home w/ Vineyard Views!

Santa Rosa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$230

Close to River & Wineries, 2BR Cottage with Hottub

Forestville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$353

Bright Modern Wine Country Hilltop Home w/ Office!

Santa Rosa house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$286

Historic Light-Filled 2BR Close to Downtown Core!

Santa Rosa house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$352

Hidden Oasis ~ a Private Luxury Home in Healdsburg

Healdsburg house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$1,794

Beautiful & Cozy Home ~ Historic Cherry Street

Santa Rosa house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$434

Cool & Calm Wine Country Home w/ Panoramic Views

Santa Rosa house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$250

Gorgeous Glen Ellen Home, Lovely Decks & Office

Glen Ellen house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$508

Wood Chalet: Dazzling, bright & Upscale! Huge windows/HotTub/Near Wineries

Guerneville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$566

Guerneville Escape: Fabulous Redwoods Retreat! Brand New Hot Tub! Pup OK!

Guerneville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$460

Bodega Breeze: Beach House w/ Studio Cottage! Privacy, Hot Tub, Walk to Beach

Bodega Bay cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$833

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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