Windsor Rentals

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104 Houses

Price per night from

$182

Price per night from

$182

Superbowl 50; February 3-10

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$574

Price per night from

$152

Sonoma Wine Nest - Location! Location! Location!

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$373

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

Windsor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$875

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

$6,881

The Stone Lodge in Kenwood ~ 5 bedroom/5 bath

Kenwood house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$4,014

Kenya's Kastle

Healdsburg house

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 8

Price per night from

$210

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

Santa Rosa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$224

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

Santa Rosa house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$480

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

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

Kenwood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$385

Cabin Compound on the Creek in the Redwoods

Cazadero log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$132

Deja Blu-Magical Ocean Front Property (Beach View)

Bodega Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$797

Price per night from

$746

Heiter House - the perfect getaway in Wine Country

Kenwood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$432

Howard's Place on the Russian River

Duncans Mills house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$442

Villa LaFleur Sonoma

Kenwood villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$2,007

Wee way - Griffin's Nest

Guerneville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$286

The Residence

Healdsburg villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

Price per night from

$2,523

Bohemian Creekside Cottage minutes from Occidental and Sebastopol

Occidental house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$343

Enchanted Forest Estate

Guerneville house

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 28

“Perfect rental for you and your 27 closest friends” I rented the Estate for my birthday april 19-21 and had 24-28 people up over the course of the weekend, and I could not be happier with my choice. The houses are quite spacious, with well appointed rooms and comfortable couches so all my guests slept well. The kitchens and common rooms are set up for large meals, and all 28 gathered for a buffet dinner in Contente with room to spare. The game rooms are the best. Everyone at the party had a blast playing ping pong, pool, air hockey, and arcade basketball. I loved walking people through the property as they arrived, as everyone was astounded by the variety of entertainments and how nice everything was. Yet, the grounds are what made this rental shine. The back deck area was a great site for my friends to gather around the grill and keg, and people loved napping on the secluded, shady lawn during the day. The private beach access is great, and when we were there, we basically had the whole segment to ourselves. My boyfriend even caught a steelhead just fishing from the beach on our second evening there. Amazing! Many of my friends said that weekend was the best birthday party they'd ever been to, and I know it is in large part because of all the wonderful features of this rental. I would love to rent this property again (after I save up for another decade)! The communication from Russian River Vacation Homes was also top notch with every email responded to within the day. Their reps are friendly and honest, and the transaction could not have been smoother.

Price per night from

$1,829

Beautiful Forest Villa Retreat in Sonoma County

Cazadero villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

Price per night from

$1,376

Alexander Valley Lodge on 54 acres with Pool and Hot Tub

Geyserville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$1,032

Grand Riverfront Estate with Dock, Minutes from the Beach

Monte Rio house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$258

Stunning Mid-Century Modern Retreat

Guerneville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$316

Tucked in between redwood trees - boho stay

Monte Rio house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$631

Luxury secluded redwood retreat in Green Valley

Forestville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$230

Studio suite in Guerneville - walk to river

Guerneville studio

  • Studio
  • 1 bathroom
  • sleeps 3

Price per night from

$172

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

Bodega Bay house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

Price per night from

$717

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

$516

Healdsburg Downtown Cottage

Healdsburg cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$287

The Cottage

Santa Rosa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$343

Tentrr Signature Site - Camp Along the Russian River

Rio Nido tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 31 minutes

Price per night from

$161

"Royal Pacific" Luxury Ocean And Golf Course Home

Bodega Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$1,090

Viewing 38 of 104
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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