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Houses in Windsor and Condos – Holiday Lettings - Holiday Rentals Windsor

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87 Holiday homes

Holiday home in Windsor

Windsor house

3 bedrooms • 2 bathrooms • sleeps 8

from £133 / night

£924 - £1,805 / week

1 / 30

Holiday home in Windsor

Windsor house

2 bedrooms • 2 bathrooms • sleeps 6

from £112 / night

£778 - £1,805 / week

1 / 22

Holiday home in Windsor

Windsor house

1 bedroom • 1 bathroom • sleeps 4

from £84 / night

£583 - £1,121 / week

1 / 27

Holiday condo with golf nearby in Windsor

Windsor condo

2 bedrooms • 2 bathrooms • sleeps 6

from £417 / night

£2,914 / week

1 / 4

Windsor holiday home rental

Windsor house

3 bedrooms • 2 bathrooms • sleeps 6

from £271 / night

£1,665 / week

1 / 11

Great rentals within 20 miles that match your search

Holiday home with swimming pool in St. Helena

St. Helena house

5 bedrooms • 8 bathrooms • sleeps 12

from £4,986 / night

£34,901 / week

1 / 22

Kenwood holiday home rental

Kenwood house

5 bedrooms • 5 bathrooms • sleeps 10

from £2,909 / night

£20,359 / week

1 / 17

Healdsburg holiday home accommodation

Healdsburg house

3 bedrooms • 6 bathrooms • sleeps 8

from £153 / night

£1,067 / week

1 / 44

Holiday cottage in Santa Rosa

Santa Rosa cottage

2 bedrooms • 1 bathroom • sleeps 6

from £162 / night

£1,226 - £1,517 / week

1 / 24

Healdsburg holiday home rental

Healdsburg house

4 bedrooms • 7 bathrooms • sleeps 8

from £1,496 / night

£8,725 / week

1 / 10

Home rental in Kenwood

Kenwood house

2 bedrooms • 2 bathrooms • sleeps 4

from £279 / night

£2,036 - £2,327 / week

1 / 24

Holiday home in Santa Rosa

Santa Rosa house

2 bedrooms • 1 bathroom • sleeps 4

from £196 / night

£1,230 - £2,188 / week

1 / 24

Holiday home in St. Helena

St. Helena house

3 bedrooms • 3 bathrooms • sleeps 6

from £209 / night

£1,561 / week

1 / 11

Holiday cottage in Petaluma

Petaluma cottage

1 bedroom • 1 bathroom • sleeps 2

from £125 / night

£750 / week

1 / 15

Sebastopol holiday home rental

Sebastopol house

3 bedrooms • 2 bathrooms • sleeps 8

from £323 / night

£2,188 - £2,480 / week

1 / 17

Cazadero holiday log cabin rental

Cazadero log cabin

2 bedrooms • 2 bathrooms • sleeps 4

from £96 / night

£671 / week

1 / 33

Holiday cottage in Healdsburg

Healdsburg cottage

2 bedrooms • 2 bathrooms • sleeps 4

from £209 / night

£1,457 / week

1 / 6

Holiday home in Kenwood

Kenwood house

2 bedrooms • 2 bathrooms • sleeps 4

from £313 / night

£1,974 / week

1 / 25

Holiday home rental

Duncans Mills house

2 bedrooms • 1 bathroom • sleeps 5

from £321 / night

£2,244 / week

1 / 21

Kenwood holiday villa rental

Kenwood villa

3 bedrooms • 3 bathrooms • sleeps 6

from £1,457 / night

£10,199 / week

1 / 17

Holiday home rental

Freestone house

4 bedrooms • 4 bathrooms • sleeps 12

from £583 / night

£4,080 / week

1 / 67

Holiday villa in Healdsburg

Healdsburg villa

4 bedrooms • 6 bathrooms • sleeps 8

from £1,832 / night

£12,821 / week

1 / 13

Holiday villa rental

Cazadero villa

4 bedrooms • 4 bathrooms • sleeps 16

from £999 / night

£6,994 / week

1 / 6

Holiday home in Penngrove

Penngrove house

3 bedrooms • 3 bathrooms • sleeps 6

from £539 / night

£3,478 / week

1 / 14

Holiday home in Geyserville

Geyserville house

6 bedrooms • 5 bathrooms • sleeps 12

from £500 / night

£2,689 - £5,378 / week

1 / 18

Holiday home in Bodega Bay

Bodega Bay house

3 bedrooms • 3 bathrooms • sleeps 7

from £666 / night

£4,656 / week

1 / 25

Glen Ellen holiday home rental

Glen Ellen house

5 bedrooms • 3 bathrooms • sleeps 10

from £834 / night

£3,753 - £5,003 / week

1 / 12

Holiday studio in Santa Rosa

Santa Rosa studio

Studio • 1 bathroom • sleeps 2

from £107 / night

£749 / week

1 / 9

Geyserville holiday farmhouse rental

Geyserville farmhouse

3 bedrooms • 2 bathrooms • sleeps 7

from £416 / night

£2,161 / week

1 / 16

Holiday home in Kenwood

Kenwood house

3 bedrooms • 3 bathrooms • sleeps 6

from £412 / night

£2,908 / week

1 / 23

Guerneville holiday home rental

Guerneville house

2 bedrooms • 2 bathrooms • sleeps 5

from £207 / night

£1,449 / week

1 / 27

Holiday home rental

Guerneville house

3 bedrooms • 2 bathrooms • sleeps 9

from £249 / night

£1,743 / week

1 / 17

Kenwood holiday home rental

Kenwood house

3 bedrooms • 3 bathrooms • sleeps 6

from £249 / night

£1,665 / week

1 / 10

Bodega Bay holiday home rental

Bodega Bay house

2 bedrooms • 2 bathrooms • sleeps 4

from £209 / night

£1,457 / week

1 / 14

Holiday home rental

Monte Rio house

1 bedroom • 1 bathroom • sleeps 4

from £121 / night

£791 / week

1 / 15

Holiday home in Occidental

Occidental house

2 bedrooms • 2 bathrooms • sleeps 9

from £208 / night

£1,451 / week

1 / 28

Home rental in Forestville

Forestville house

1 bedroom • 1 bathroom • sleeps 2

from £158 / night

£1,102 / week

1 / 15

Holiday guest house in Sebastopol

Sebastopol guest house

1 bedroom • 1 bathroom • sleeps 3

from £137 / night

£956 / week

1 / 22

Home rental in Forestville

Forestville house

1 bedroom • 1 bathroom • sleeps 4

from £333 / night

£2,325 / week

1 / 42

Bodega Bay holiday home rental

Bodega Bay house

4 bedrooms • 4 bathrooms • sleeps 12

from £791 / night

£5,536 / week

1 / 15

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Windsor holidays

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, jewellery, and crafts are easy to find. Visitors will also encounter a cornucopia of fruits, vegetables, and home-grown 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 holiday 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 travellers 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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