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Windsor Rentals

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89 Houses

Responds fast! avg. 3 hours 31 minutes

Price per night from

$179

Responds fast! avg. 3 hours 31 minutes

Price per night from

$160

Superbowl 50; February 3-10

Windsor condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$571

Responds fast! avg. 3 hours 31 minutes

Price per night from

$139

Sonoma Wine Nest - Location! Location! Location!

Windsor house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$371

Great rentals within 20 miles that match your search

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

$6,843

The Stone Lodge in Kenwood ~ 5 bedroom/5 bath

Kenwood house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$3,992

Kenya's Kastle

Healdsburg house

3 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$209

Sally's Garden Cottage, Sleeps 2-6, Walk to Shops

Santa Rosa cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$223

The TreeHouse- Charming Cabin in the Redwoods

Monte Rio house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$166

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

Kenwood house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$382

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

Santa Rosa house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$477

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

$285

Lovely Country Cottage in Heart of Wine Country

Petaluma cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$171

Deja Blu-Magical Ocean Front Property (Beach View)

Bodega Bay house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 1 hour 56 minutes

Price per night from

$793

Cabin Compound on the Creek in the Redwoods

Cazadero log cabin

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$132

AMAZING cottage! Perfectly located in Santa Rosa

Santa Rosa studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 8 minutes

Price per night from

$148

Healdsburg Downtown Cottage

Healdsburg cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$285

Heiter House - the perfect getaway in Wine Country

Kenwood house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$429

Hillside Vineyard Estate on 6 Gated Acres Beautiful Retreat with Amazing Views

Penngrove house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$742

Howard's Place on the Russian River

Duncans Mills house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 40 minutes

Price per night from

$439

Villa LaFleur Sonoma

Kenwood villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$1,996

The Residence

Healdsburg villa

4 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$2,509

Wee way - Griffin's Nest

Guerneville house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$284

Bohemian Creekside Cottage minutes from Occidental and Sebastopol

Occidental house

2 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$341

Beautiful Forest Villa Retreat in Sonoma County

Cazadero villa

4 bedrooms / 4 bathrooms / sleeps 16

Price per night from

$1,369

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

Studio suite in Guerneville - walk to river

Guerneville studio

Studio / 1 bathroom / sleeps 3

Price per night from

$171

WALK to Wineries from this Gorgeous Designer Home!

Kenwood house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$565

Spectacular Ocean Views! ****SPECIAL Stay 4 Nights & The 5th Night is FREE

Bodega Bay house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 minutes

Price per night from

$679

"Royal Pacific" Luxury Ocean And Golf Course Home

Bodega Bay house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 44 minutes

Price per night from

$1,084

Healdsburg Relaxing Wine Country Farmhouse

Forestville farmhouse

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$343

Secluded Hillside Hideaway Offers Elegance/Comfort

Forestville house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$257

Healdsburg Home with Magnificent Vineyard View

Healdsburg house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 42 minutes

Price per night from

$417

Tentrr Signature Site - Mystic Mountain Petrified Camp

Calistoga tented camp

1 bedroom / 1 bathroom / sleeps 10

Price per night from

$138

Viewing 38 of 89
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.

Top Destination reviews

Windsor, CA Cottage in Sonoma's Wine Country
Perfect Location-quaint and sweet

Just outside of Windsor and only a 10 min drive to Healdsburg, what a great place to stay. Roomy, light, and the kitchen was really convienient. The proprieter is so nice, and helped steer us to the best wineries! You can't go wrong. And the price is right. :) … see more

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