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Windsor Rentals

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age 0-16
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320 Houses

Stunning vineyard views from the private deck at this wine-lovers house!

Windsor house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$518

Price per night from

$259

Windsor, CA Cottage in Sonoma's Wine Country

Windsor cottage

2 bedrooms / 1 bathroom / sleeps 4

“Exactly what we were looking for!” My fiancee and I rented the Carriage House with another couple on Labor Day weekend. This space was great for that circumstance and would also be great for a family. First of all, the location of the Carriage House is fantastic. There are tons of good wineries within biking distance and it is within walking distance to the quaint downtown area of Windsor which offers restaurants and boutique shops. The Carriage House itself is very comfortable (beds are fantastic), clean and there are even areas to sit outside and relax. The decor is stylish and thoughtful. A washer and dryer, darling kitchenette with a full sized fridge and plenty of parking are included in the amenities. The best part of the experience was our hosts, Justine and Eustacio. They were very welcoming, gracious and hospitable. We had great conversations with them during our stay and they were helpful in suggesting good places to eat, etc.

Price per night from

$347

Price per night from

$192

Wine Country Townhouse

Windsor house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$397

Worldmark Windsor Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

Windsor condo

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$463

Superbowl 50; February 3-10

Windsor condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$579

Price per night from

$154

Price per night from

$463

Price per night from

$463

Close to Healdsburg Plaza with Vineyard Views!

Windsor house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$405

Price per night from

$463

Worldmark Windsor #5Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

Windsor condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$463

Price per night from

$463

Sonoma county attached two bedroom cottage

Windsor guest house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$231

Price per night from

$463

Price per night from

$324

Price per night from

$463

Price per night from

$463

Great rentals within 20 miles that match your search

Casa Blanca

Glen Ellen house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$921

"Royal Pacific" Luxury Ocean And Golf Course Home

Bodega Bay house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 24 minutes

Price per night from

$897

Secluded Hillside Hideaway Offers Elegance/Comfort

Forestville house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$214

Tree house Hideaway

Guerneville house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$230

Romantic Wine Country Get-a-way

Sebastopol cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$249

Ranch Home in the Heart of Napa Valley Vineyards

St. Helena house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 18 minutes

Price per night from

$249

Beautiful mountain top wine retreat in Healdsburg!

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$405

Warm & Cozy 1927 Riverfront Home and Gardens

Monte Rio house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$577

Pet Friendly Lake Sonoma Ranch House on 35 Acres with Water and Mountain Views

Geyserville house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$853

Velouria - Hot Tub, Woodstove, Redwoods.

Guerneville log cabin

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$196

Wine Country Retreat - Elegant & Comfortable Home

Kenwood house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$346

WALK to Wineries from this Gorgeous Designer Home!

Kenwood house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 minutes

Price per night from

$572

Owl Hill Cottage- In the West Sonoma Wine Country

Sebastopol house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$226

Riverdale - Spacious and Comfy Property on the Russian River, Hot Tub!

Monte Rio house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$328

Little Bird Cottage, Perfectly Located

Sebastopol cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$203

Have an Adventure not Just a Place~Comfort and Camping~the Best of Both Worlds

Geyserville beach hut

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$145

Good view

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$654

Healdsburg Contemporary Cottage

Healdsburg house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$348

Stunning Mountain Top Estate with View Over Dry Creek Vineyards

Healdsburg villa

3 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 1 hour 21 minutes

Price per night from

$983

Viewing 38 of 320
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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