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

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149 Holiday homes

Windsor holiday cottage rental

Windsor cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £139 / night

£970 / week

1 / 15

Holiday home in Windsor

Windsor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £153 / night

£1,067 / week

1 / 4

Holiday home in Windsor

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £196 / night

£1,374 - £2,064 / week

1 / 30

Holiday home in Windsor

Windsor house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £156 / night

£1,087 - £3,500 / week

1 / 22

Holiday home with indoor pool in Windsor

Windsor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £475 / night

£2,884 / week

1 / 49

Holiday condo with golf nearby in Windsor

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £462 / night

£3,233 / week

1 / 4

Holiday home in Windsor

Windsor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £147 / night

£1,029 - £2,581 / week

1 / 27

Windsor holiday home rental

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £301 / night

£1,848 / week

1 / 11

Holiday condo rental

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £201 / night

£1,406 / week

1 / 19

Holiday home in Windsor

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £214 / night

£1,497 / week

1 / 16

Holiday home in Windsor

Windsor house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £209 / night

£1,463 / week

1 / 23

Holiday condo in Windsor

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £141 / night

£983 / week

1 / 20

Holiday home accommodation

Windsor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £554 / night

£3,874 / week

1 / 22

Holiday home in Windsor

Windsor house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £209 / night

£1,463 / week

1 / 23

Home rental in Windsor

Windsor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £463 / night

£3,241 / week

1 / 23

Home rental in Windsor

Windsor house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £404 / night

£2,824 / week

1 / 21

Windsor holiday condo let

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £186 / night

£1,299 / week

1 / 24

Windsor holiday home rental

Windsor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £172 / night

£1,203 / week

1 / 21

Holiday home in Windsor

Windsor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £289 / night

£2,022 / week

1 / 21

Holiday cottage in Windsor

Windsor cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £140 / night

£977 / week

1 / 30

Holiday home in Windsor

Windsor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £670 / night

£4,687 / week

1 / 30

Windsor holiday home let

Windsor house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £185 / night

£1,293 / week

1 / 23

Holiday home in Windsor

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £210 / night

£1,468 / week

1 / 26

Holiday cottage in Windsor

Windsor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £198 / night

£1,384 / week

1 / 23

Holiday home in Windsor

Windsor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £500 / night

£3,501 / week

1 / 25

Holiday home in Windsor

Windsor house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £873 / night

£6,110 / week

1 / 30

Holiday home rental

Windsor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £99 / night

£689 / week

1 / 14

Holiday home in Windsor

Windsor house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £362 / night

£2,530 / week

1 / 30

Home rental in Windsor

Windsor house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £390 / night

£2,728 / week

1 / 30

Condo rental in Windsor

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £191 / night

£1,333 / week

1 / 12

Windsor holiday home rental

Windsor house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £206 / night

£1,440 / week

1 / 23

Windsor ski home to rent.

Windsor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £480 / night

£3,360 / week

1 / 30

Condo rental in Windsor

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £178 / night

£1,243 / week

1 / 11

Home accommodation in Windsor

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £491 / night

£3,433 / week

1 / 21

Holiday home letting

Windsor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £283 / night

£1,977 / week

1 / 30

Holiday home in Windsor

Windsor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £413 / night

£2,886 / week

1 / 25

Windsor holiday home rental

Windsor house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £347 / night

£2,428 / week

1 / 30

Holiday home in Windsor

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £201 / night

£1,406 / week

1 / 25

Holiday home rental

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £223 / night

£1,559 / week

1 / 25

Holiday home rental

Windsor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from £319 / night

£2,231 / week

1 / 30

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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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