Windsor Rentals

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114 Houses

Responds fast! avg. 1 hour 51 minutes

Price per night from

$243

Responds fast! avg. 1 hour 51 minutes

Price per night from

$172

Superbowl 50; February 3-10

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$573

Responds fast! avg. 1 hour 51 minutes

Price per night from

$172

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

$189

With Pool & Hot Tub, Beautifully Appointed 4BR Home!

Windsor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$593

Great rentals within 20 miles that match your search

Cabin Compound on the Creek in the Redwoods

Cazadero log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$132

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

Kenwood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$384

Healdsburg, 4BR/3BA, Hot tub, Fire pit, Vineyard views

Healdsburg house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,031

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

Santa Rosa house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$479

Spacious Studio in Sonoma wine country

Santa Rosa studio

  • Studio
  • 1 bathroom
  • sleeps 3

Price per night from

$218

Urban Retreat in the Heart of St. Helena

St. Helena house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$287

Lovely Country Cottage in Heart of Wine Country

Petaluma cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$172

Healdsburg, 5BR/5.5BA Estate, Pool, Hot tub, Fire pit, Games

Healdsburg house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$3,321

Healdsburg, 4BR/2.5BA, hot tub, Fire pit, Bocce Ball, BBQ

Healdsburg house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,031

Sweet Creek Russian River Vacation Wonderland

Monte Rio house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$258

Deja Blu-Magical Ocean Front Property (Beach View)

Bodega Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$911

"Royal Pacific" Luxury Ocean And Golf Course Home

Bodega Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$1,088

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

$1,827

Healdsburg, Jimtown, 3BR/2BA, hot tub, Internet, BBQ, Gardens

Healdsburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Difficult to reserve, but beautiful property” We recently stayed at the Jimtown house with 2 other couples. We had a great time enjoying the lovely house. The hard work came before when trying to make the reservations. We found the property management to be polite, but irritating. They sent a 12 page contract with an ridiculous amount to signatures required. They didn't answer repeated questions and the payment process was very unprofessional. They asked for my credit card information through email. They require you to open a special account to pay for the security deposit. It has been 2 weeks and I haven't seen my deposit returned yet. They require you to pay a cleaning fee of $200 and then ask you to clean the house before you leave. We had to empty waste baskets, sweep and remove linens from the bed. The house itself is beautifully furnished and very clean. It is close to the road so there is road noise, but we loved the surrounding and the gardens. The irrigation to the garden in back was out of order so we hand watered the trees and veggies because they were literally dying. Hopefully the owners were alerted and fixed it because the garden is great If the management company were different, I would have given 5 stars, but they need to revamp their system to make it easier for their clients to rent the house!

Price per night from

$745

WALK to Wineries from this Gorgeous Designer Home!

Kenwood house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$567

Ranch Home in the Heart of Napa Valley Vineyards

St. Helena house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$802

Secluded Hillside Hideaway Offers Elegance/Comfort

Forestville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$257

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

$6,870

The Stone Lodge in Kenwood ~ 5 bedroom/5 bath

Kenwood house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$4,008

Kenya's Kastle

Healdsburg house

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 8

Price per night from

$210

The TreeHouse- Charming Cabin in the Redwoods

Monte Rio house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$189

Howard's Place on the Russian River

Duncans Mills house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$441

Villa LaFleur Sonoma

Kenwood villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$2,004

Healdsburg, 4BR/4BA, Pool, Internet, Fireplace

Healdsburg house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,603

Heiter House - the perfect getaway in Wine Country

Kenwood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$431

Price per night from

$682

Price per night from

$745

Romantic Wine Country Cottage with View, Hot Tub & Pool

Sebastopol guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$188

Wine Country Retreat - Elegant & Comfortable Home

Kenwood house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$343

Healdsburg Downtown Cottage

Healdsburg cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$287

Viewing 38 of 114
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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