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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

$355

Price per night from

$240

Superbowl 50; February 3-10

Windsor condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$654

Price per night from

$220

Sonoma Wine Nest - Location! Location! Location!

Windsor house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$376

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

Windsor house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$424

Corner-Lot Beauty | Gourmet Kitchen | Fenced Yard with Private Hot Tub

Windsor house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$484

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

Windsor house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$530

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

$197

Urban Retreat in the Heart of St. Helena

St. Helena house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$327

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

Santa Rosa cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$256

The Residence

Healdsburg villa

4 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$2,878

Healdsburg Downtown Cottage

Healdsburg cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$327

The Ultimate Wine County View Estate

Healdsburg house

4 bedrooms / 7 bathrooms / sleeps 8

Price per night from

$1,090

Cabin Compound on the Creek in the Redwoods

Cazadero log cabin

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$151

Kenya's Kastle

Healdsburg house

3 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$240

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

Penngrove house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$851

Heiter House - the perfect getaway in Wine Country

Kenwood house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$324

Beautiful mountain top wine retreat in Healdsburg!

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 22 minutes

Price per night from

$431

Spectacular Sonoma Estate

Freestone house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 36 minutes

Price per night from

$816

Secluded Wine Country Home - 2 acre Orchard Estate

Sebastopol house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$450

Howard's Place on the Russian River

Duncans Mills house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 5 minutes

Price per night from

$432

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

Kenwood house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$377

Beautiful Forest Villa Retreat in Sonoma County

Cazadero villa

4 bedrooms / 4 bathrooms / sleeps 16

Price per night from

$1,350

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

Santa Rosa house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$202

Deja Blu-Magical Ocean Front Property (Beach View)

Bodega Bay house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 3 hours 19 minutes

Price per night from

$781

Villa LaFleur Sonoma

Kenwood villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Price per night from

$2,025

AMAZING cottage! Perfectly located in Santa Rosa

Santa Rosa studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 4 minutes

Price per night from

$148

"Royal Pacific" Luxury Ocean And Golf Course Home

Bodega Bay house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 1 minutes

Price per night from

$1,084

Casa Blanca

Glen Ellen house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,141

WALK to Wineries from this Gorgeous Designer Home!

Kenwood house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$566

Spacious Studio in Sonoma wine country

Santa Rosa studio

Studio / 1 bathroom / sleeps 3

Price per night from

$217

The TreeHouse- Charming Cabin in the Redwoods

Monte Rio house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$166

Oceanfront Gem w/ Stunning Panorama, Goat Rock SB

Bodega Bay house

3 bedrooms / 1 bathroom / sleeps 6

“Great Coast Property” Outstanding views from this house and deck. Very cozy place to come in from the cold after long days of exploring coast and Russian river. Clean and well kept house, doesn't feel like a rental. Can't wait to come back.

Responds fast! avg. 2 hours 40 minutes

Price per night from

$395

Mandolin Wind - Private retreat with hot tub and partial ocean view

Bodega Bay house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$287

Tree house Hideaway

Guerneville house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 3 hours 23 minutes

Price per night from

$343

Cosmo Beach Riverfront Sanctuary

Forestville house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 30 minutes

Price per night from

$457

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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