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

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91 Holiday homes

Holiday home in Windsor

Windsor house

3 bedrooms / 2 bathrooms / sleeps 8

from £206 / night

£1,442 - £1,924 / week

Holiday home in Windsor

Windsor house

2 bedrooms / 2 bathrooms / sleeps 6

from £158 / night

£1,105 - £1,779 / week

Holiday condo with golf nearby in Windsor

Windsor condo

2 bedrooms / 2 bathrooms / sleeps 6

from £471 / night

£3,294 / week

Holiday home in Windsor

Windsor house

1 bedroom / 1 bathroom / sleeps 4

from £131 / night

£911 - £1,442 / week

Windsor holiday home rental

Windsor house

3 bedrooms / 2 bathrooms / sleeps 6

from £288 / night

£1,770 / week

Great rentals within 20 miles that match your search

Holiday cottage in Petaluma

Petaluma cottage

1 bedroom / 1 bathroom / sleeps 2

1

from £142 / night

£848 / week

Holiday home in St. Helena

St. Helena house

3 bedrooms / 3 bathrooms / sleeps 6

from £236 / night

£1,765 / week

Holiday cottage in Santa Rosa

Santa Rosa cottage

2 bedrooms / 1 bathroom / sleeps 6

1

from £184 / night

£1,389 - £1,718 / week

Holiday villa in Healdsburg

Healdsburg villa

4 bedrooms / 6 bathrooms / sleeps 8

from £2,071 / night

£14,496 / week

Holiday cottage in Healdsburg

Healdsburg cottage

2 bedrooms / 2 bathrooms / sleeps 4

from £236 / night

£1,648 / week

Healdsburg holiday home rental

Healdsburg house

4 bedrooms / 7 bathrooms / sleeps 8

from £1,694 / night

£9,882 / week

Cazadero holiday log cabin rental

Cazadero log cabin

2 bedrooms / 2 bathrooms / sleeps 4

from £109 / night

£758 / week

Healdsburg holiday home accommodation

Healdsburg house

3 bedrooms / 6 bathrooms / sleeps 8

from £173 / night

£1,208 / week

Holiday home in Penngrove

Penngrove house

3 bedrooms / 3 bathrooms / sleeps 6

from £612 / night

£3,953 / week

Holiday home in Santa Rosa

Santa Rosa house

3 bedrooms / 3 bathrooms / sleeps 6

from £282 / night

£1,970 / week

Holiday home in Kenwood

Kenwood house

2 bedrooms / 2 bathrooms / sleeps 4

6

from £233 / night

£1,468 - £5,647 / week

Holiday home in Santa Rosa

Santa Rosa house

2 bedrooms / 1 bathroom / sleeps 4

2

from £167 / night

£1,052 - £2,220 / week

Kenwood holiday villa rental

Kenwood villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

from £1,626 / night

£11,379 / week

Holiday home in Sebastopol

Sebastopol house

3 bedrooms / 2 bathrooms / sleeps 8

5

from £133 / night

£795 - £1,723 / week

Home rental in Healdsburg

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

1

Responds fast! avg. 22 minutes

from £310 / night

£2,211 - £2,582 / week

Forestville holiday villa rental

Forestville villa

5 bedrooms / 3 bathrooms / sleeps 10

from £1,127 / night

£6,614 / week

Home rental in Kenwood

Kenwood house

2 bedrooms / 2 bathrooms / sleeps 4

1

from £289 / night

£2,114 - £2,415 / week

Sebastopol holiday studio rental

Sebastopol studio

Studio / 1 bathroom / sleeps 2

from £112 / night

£782 / week

Holiday home with swimming pool in Sebastopol

Sebastopol house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 18 minutes

from £443 / night

£3,098 / week

Holiday b&b in Santa Rosa

Santa Rosa b&b

3 bedrooms / 1 bathroom / sleeps 6

from £230 / night

£1,444 - £2,277 / week

Holiday home in Freestone

Freestone house

2 bedrooms / 1 bathroom / sleeps 4

1

Responds fast! avg. 2 hours 27 minutes

from £196 / night

£1,369 / week

Holiday home rental

Freestone house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 36 minutes

from £587 / night

£4,108 / week

Holiday cottage in Sebastopol

Sebastopol cottage

1 bedroom / 1 bathroom / sleeps 3

5

from £144 / night

£782 - £926 / week

Holiday home rental

Duncans Mills house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 6 minutes

from £317 / night

£2,218 / week

Holiday cottage in Santa Rosa

Santa Rosa cottage

1 bedroom / 1 bathroom / sleeps 4

1

from £115 / night

£707 - £938 / week

Home rental in Healdsburg with golf nearby

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 9

from £1,494 / night

£10,454 / week

Sebastopol holiday home rental

Sebastopol house

3 bedrooms / 2 bathrooms / sleeps 8

1

from £324 / night

£2,190 - £2,482 / week

Holiday home in Geyserville

Geyserville house

6 bedrooms / 5 bathrooms / sleeps 12

from £578 / night

£4,322 - £5,153 / week

Holiday villa in Healdsburg

Healdsburg villa

3 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 3 hours 33 minutes

from £705 / night

£4,933 / week

Geyserville holiday farmhouse rental

Geyserville farmhouse

3 bedrooms / 2 bathrooms / sleeps 7

3

from £414 / night

£2,151 / week

Holiday studio in Santa Rosa

Santa Rosa studio

Studio / 1 bathroom / sleeps 2

5

Responds fast! avg. 4 minutes

from £107 / night

£747 / week

Holiday cottage with shared pool, golf nearby in Kenwood

Kenwood cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 41 minutes

from £187 / night

£1,303 / week

Holiday home in Bodega Bay

Bodega Bay house

3 bedrooms / 3 bathrooms / sleeps 7

4

Responds fast! avg. 3 hours 4 minutes

from £538 / night

£2,896 / week

Home rental in Forestville

Forestville house

1 bedroom / 1 bathroom / sleeps 2

from £124 / night

£863 / week

Viewing 39 of 91
rentals in Windsor

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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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