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354 Houses

22

1BD Worldmark Windsor Condo

Sonoma County / Windsor

Windsor condo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ask about children

Price per night from

$115

Price per night from

$115

(1) Excellent 

26

Sonoma Wine Country Suite

Sonoma County / Windsor

Windsor house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$160

Price per night from

$160

30

Windsor, CA: Sonoma 3 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!

Sonoma County / Windsor

Windsor house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly

Price per night from

$209

Price per night from

$209

(6) Excellent 

21

Windsor, CA Cottage in Sonoma's Wine Country

Sonoma County / Windsor

Windsor cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 35 mi
  • Child Friendly
  • Car not necessary
“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
…see more

Price per night from

$301

Price per night from

$301

14

2BD WorldMark Windsor Condo

Sonoma County / Windsor

Windsor condo

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Ask about children

Price per night from

$136

Price per night from

$136

22

Windsor, CA: Sonoma 2 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!

Sonoma County / Windsor

Windsor house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$150

Price per night from

$150

(3) Average 

11

Wine Country Townhouse

Sonoma County / Windsor

Windsor house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$344

Price per night from

$344

4

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

Sonoma County / Windsor

Windsor condo

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$401

Price per night from

$401

27

Windsor, CA: Sonoma 1 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!

Sonoma County / Windsor

Windsor house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly

Price per night from

$125

Price per night from

$125

4

Worldmark Windsor #10 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

Sonoma County / Windsor

Windsor condo

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$401

Price per night from

$401

4

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

Sonoma County / Windsor

Windsor condo

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$401

Price per night from

$401

4

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

Sonoma County / Windsor

Windsor condo

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$400

Price per night from

$400

4

Superbowl 50; February 3-10

Sonoma County / Windsor

Windsor condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly

Price per night from

$501

Price per night from

$501

4

Worldmark Windsor # 9 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

Sonoma County / Windsor

Windsor condo

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$401

Price per night from

$401

15

Close to Healdsburg Plaza with Vineyard Views!

Sonoma County / Windsor

Windsor house

3 9 2 nights min

  • 3 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$351

Price per night from

$351

4

Worldmark Windsor # 8 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

Sonoma County / Windsor

Windsor condo

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$401

Price per night from

$401

4

Worldmark Windsor #4 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

Sonoma County / Windsor

Windsor condo

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$400

Price per night from

$400

4

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

Sonoma County / Windsor

Windsor condo

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$281

Price per night from

$281

4

Worldmark Windsor #6 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

Sonoma County / Windsor

Windsor condo

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$401

Price per night from

$401

41

Wine country escape

Sonoma County / Windsor

Windsor house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min

Price per night from

$351

Price per night from

$351

4

Worldmark Windsor # 7 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

Sonoma County / Windsor

Windsor condo

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$401

Price per night from

$401

7

Wine Country Condo #8121

Sonoma County / Windsor

Windsor condo

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$465

Responds fast!
avg. 3 hours 26 minutes

Price per night from

$465

Great rentals within 20 miles that match your search

Distance approx 19.73 km from Windsor

(12) Excellent 

25

Harbor Cutie, Breathtaking Bay View, Charming Home

Sonoma County / Bodega Bay

Bodega Bay house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Child Friendly
“mary kaplan” Our family(5 adults and 2 kids) spend the labor day weekend weekend at the house.Was very clean, convinient,childproof. Very close to hiking trails and beaches.We cooked all meals, also did some bbq. Everybody had a good time, the owner
…see more

Price per night from

$246

Responds fast!
avg. 1 hour 4 minutes

Price per night from

$246

Distance approx 17.92 km from Windsor

(3) Excellent 

17

The Viking House at Jenner-Riverfront Great Views

Sonoma County / Jenner

Jenner house

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Pet Friendly

Price per night from

$401

Price per night from

$401

Distance approx 15.12 km from Windsor

(1) Excellent 

11

Riverside Retreat - Picturesque, Riverfront Cottage, Hot Tub

Sonoma County / Duncans Mills

Duncans Mills house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$210

Price per night from

$210

Distance approx 10.25 km from Windsor

10

Russian River Retreat

Sonoma County / Guerneville

Guerneville house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$251

Price per night from

$251

Distance approx 18.94 km from Windsor

(1) Excellent 

9

Recently Remodeled1 Bedroom Apartment near Downto

Napa Valley / St. Helena

St. Helena apartment

1 4 30 nights min

  • 1 bedroom
  • sleeps 4
  • 30 nights min
  • Nearest beach 97 mi
  • Air conditioning
  • Private garden

Price per night from

$109

Price per night from

$109

Distance approx 6.51 km from Windsor

(19) Very Good 

22

PEACE & QUIET: Wine Tasting | Fireplace | Hot Tub

Sonoma County / Forestville

Forestville house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Pet Friendly
“Very happy with Peace and Quiet” Could not have been better. House was exactly as described -- plus immaculate and very well equipped. Absolutely wonderful experience staying there!
…see more

Price per night from

$260

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$260

Distance approx 12.63 km from Windsor

29

Vista Point at Llano Road

Sonoma County / Santa Rosa

Santa Rosa house

4 9 3 nights min

  • 4 bedrooms
  • sleeps 9
  • 3 nights min
  • Nearest beach 35 mi
  • Child Friendly
  • Private garden

Price per night from

$376

Price per night from

$376

Distance approx 19.71 km from Windsor

17

New home on Sonoma Creek and Mountain Views Minutes from wine tasting and Dining

Sonoma County / Glen Ellen

Glen Ellen house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$706

Price per night from

$706

Distance approx 16.58 km from Windsor

9

Bella Luna Suite at Casa Bella

Sonoma County / Kenwood

Kenwood cottage

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$302

Price per night from

$302

Distance approx 17.49 km from Windsor

14

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

Sonoma County / Penngrove

Penngrove house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Air conditioning
  • Private garden

Price per night from

$651

Price per night from

$651

Distance approx 5.26 km from Windsor

(7) Average 

14

Wine Country Cottage

Sonoma County / Healdsburg

Healdsburg house

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
“Nice cottage in a cute wine country location” We loved staying here, it was comfy, cozy and walking distance to the cute little town of Healdsburg. It had all the amenities we needed and the cottage was very comfy and we had a blast hanging out in th
…see more

Price per night from

$402

Price per night from

$402

Distance approx 10.78 km from Windsor

(1) Very Good 

9

Sonoma County Living ~ Casual Elegance

Sonoma County / Santa Rosa

Santa Rosa house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 20 mi
  • Air conditioning
  • Private garden

Price per night from

$136

Responds fast!
avg. 3 hours 39 minutes

Price per night from

$136

Distance approx 5.48 km from Windsor

44

Kenya's Kastle

Sonoma County / Healdsburg

Healdsburg house

3 8 30 nights min

  • 3 bedrooms
  • sleeps 8
  • 30 nights min
  • Child Friendly

Price per night from

$185

Price per night from

$185

Distance approx 9.13 km from Windsor

20

Midcentury Cabin in the Redwoods

Sonoma County / Forestville

Forestville house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$281

Price per night from

$281

Distance approx 9.5 km from Windsor

22

STARRY PLOUGH: Riverfront | Firepit | Close 2 Town

Sonoma County / Guerneville

Guerneville house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$240

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$240

Distance approx 4.26 km from Windsor

16

Russian River Valley "Calmpound"

Sonoma County / Healdsburg

Healdsburg guest house

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$201

Responds fast!
avg. 3 hours 45 minutes

Price per night from

$201

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.