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Windsor Rentals

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161 Results

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Price: high to low

Number of reviews

161 Houses

Price per night from

$288

Price per night from

$220

Superbowl 50; February 3-10

Windsor condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$645

Price per night from

$182

Sonoma Wine Nest - Location! Location! Location!

Windsor house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$394

Spacious Wine Country Getaway w/ Private Backyard, Updated Kitchen & AC

Windsor house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$424

Elegant Creek-Side Home with Large Deck, Fenced Yard & Private Hot Tub

Windsor house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$466

Great rentals within 20 miles that match your search

Lovely Country Cottage in Heart of Wine Country

Petaluma cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$194

Urban Retreat in the Heart of St. Helena

St. Helena house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$323

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

Santa Rosa cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$252

The Residence

Healdsburg villa

4 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$2,839

Healdsburg Downtown Cottage

Healdsburg cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$323

The Ultimate Wine County View Estate

Healdsburg house

4 bedrooms / 7 bathrooms / sleeps 8

Price per night from

$1,075

Cabin Compound on the Creek in the Redwoods

Cazadero log cabin

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$149

Kenya's Kastle

Healdsburg house

3 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$236

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

Penngrove house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$839

Skyhawk Dream with View

Santa Rosa house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$386

Heiter House - the perfect getaway in Wine Country

Kenwood house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$320

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

Santa Rosa house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$229

Villa LaFleur Sonoma

Kenwood villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$2,228

Cumbria Guest House Sebastopol

Sebastopol house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$364

Beautiful mountain top wine retreat in Healdsburg!

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 22 minutes

Price per night from

$425

Fabulous Sonoma 4-5 Bedroom Estate & Vineyard - EVENTS-POOL-SPA

Forestville villa

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,545

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

Kenwood house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$396

Apple Blossom Retreat

Sebastopol studio

Studio / 1 bathroom / sleeps 2

Price per night from

$153

Modern West Sonoma Home on 2 Acres w/ Sound System

Sebastopol house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 18 minutes

Price per night from

$607

Downtown, 3 bdrms close to Pliny and Great food

Santa Rosa b&b

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$314

Cozy Sebastopol Townhome on a Pinot Noir Vineyard!

Freestone house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 27 minutes

Price per night from

$268

Spectacular Sonoma Estate

Freestone house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 36 minutes

Price per night from

$805

Little Bird Cottage, Perfectly Located

Sebastopol cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$198

Howard's Place on the Russian River

Duncans Mills house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 6 minutes

Price per night from

$435

Wine Country Retreat

Santa Rosa cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$157

Secluded Wine Country Home - 2 acre Orchard Estate

Sebastopol house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$442

Alexander Valley Lodge on 54 acres with Pool and Hot Tub

Geyserville house

6 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$794

Dreamy Wine Country Family Estate

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 9

Price per night from

$2,047

Cozy Cottage by the River ***Pet Friendly***

Forestville house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$171

The TreeHouse- Charming Cabin in the Redwoods

Monte Rio house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 56 minutes

Price per night from

$160

Viewing 37 of 161
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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