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

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270 Holiday homes

Windsor holiday home rental

Windsor house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 0 minutes

from £422 / night

£2,952 / week

Holiday home in Windsor

Windsor house

3 bedrooms / 2 bathrooms / sleeps 8

from £213 / night

£1,489 / week

Holiday cottage in Windsor

Windsor cottage

2 bedrooms / 1 bathroom / sleeps 4

6

from £283 / night

£1,694 / week

Holiday home in Windsor

Windsor house

2 bedrooms / 2 bathrooms / sleeps 6

from £158 / night

£1,102 - £1,876 / week

Windsor holiday home rental

Windsor house

3 bedrooms / 3 bathrooms / sleeps 6

3

from £323 / night

£2,259 / week

Holiday condo in Windsor

Windsor condo

3 bedrooms / 2 bathrooms / sleeps 8

from £377 / night

£2,636 / 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 £127 / night

£880 - £1,655 / week

Holiday condo rental

Windsor condo

3 bedrooms / 2 bathrooms / sleeps 6

from £377 / night

£2,636 / week

Condo rental in Windsor

Windsor condo

3 bedrooms / 2 bathrooms / sleeps 8

from £377 / night

£2,636 / week

Windsor holiday condo rental

Windsor condo

3 bedrooms / 2 bathrooms / sleeps 6

from £377 / night

£2,636 / week

Condo rental in Windsor

Windsor condo

3 bedrooms / 2 bathrooms / sleeps 6

from £377 / night

£2,636 / week

Home rental in Windsor

Windsor house

3 bedrooms / 3 bathrooms / sleeps 8

2

from £330 / night

£2,306 / week

Holiday condo rental

Windsor condo

3 bedrooms / 2 bathrooms / sleeps 6

from £377 / night

£2,636 / week

Guest house rental in Windsor

Windsor guest house

2 bedrooms / 1 bathroom / sleeps 4

from £189 / night

£1,318 / week

Condo rental in Windsor

Windsor condo

3 bedrooms / 2 bathrooms / sleeps 8

from £377 / night

£2,636 / week

Windsor holiday condo rental

Windsor condo

3 bedrooms / 2 bathrooms / sleeps 8

from £263 / night

£1,842 / week

Condo rental in Windsor

Windsor condo

3 bedrooms / 2 bathrooms / sleeps 8

from £377 / night

£2,636 / week

Holiday condo rental

Windsor condo

3 bedrooms / 2 bathrooms / sleeps 6

from £377 / night

£2,636 / week

Great rentals within 20 miles that match your search

Monte Rio holiday home rental

Monte Rio house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 25 minutes

from £304 / night

£2,125 / week

Glen Ellen holiday home rental

Glen Ellen house

5 bedrooms / 3 bathrooms / sleeps 10

from £749 / night

£3,369 - £5,240 / week

Bodega Bay holiday home rental

Bodega Bay house

4 bedrooms / 4 bathrooms / sleeps 12

1

Responds fast! avg. 3 hours 24 minutes

from £729 / night

£4,374 / week

Holiday home in Forestville

Forestville house

2 bedrooms / 1 bathroom / sleeps 4

2

from £174 / night

£1,195 / week

Holiday home rental

Guerneville house

3 bedrooms / 2 bathrooms / sleeps 9

1

from £187 / night

£1,309 / week

Holiday cottage in Sebastopol

Sebastopol cottage

1 bedroom / 1 bathroom / sleeps 4

2

from £155 / night

£931 - £1,259 / week

Home rental in St. Helena with golf nearby

St. Helena house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 18 minutes

from £202 / night

£1,527 / week

Home rental in Healdsburg

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

1

from £329 / night

£2,349 - £2,744 / week

Monte Rio holiday home rental

Monte Rio house

3 bedrooms / 3 bathrooms / sleeps 6

2

from £469 / night

£3,282 - £5,255 / week

Home accommodation in Geyserville

Geyserville house

3 bedrooms / 3 bathrooms / sleeps 8

from £694 / night

£4,369 / week

Holiday log cabin in Guerneville

Guerneville log cabin

2 bedrooms / 1 bathroom / sleeps 4

from £159 / night

£1,000 / week

Holiday cottage in Santa Rosa

Santa Rosa cottage

1 bedroom / 1 bathroom / sleeps 3

5

Responds fast! avg. 44 minutes

from £112 / night

£783 / week

Kenwood holiday home rental

Kenwood house

3 bedrooms / 3 bathrooms / sleeps 6

from £281 / night

£1,879 / week

Holiday home in Kenwood

Kenwood house

3 bedrooms / 3 bathrooms / sleeps 6

4

Responds fast! avg. 2 hours 58 minutes

from £465 / night

£3,288 - £5,529 / week

Holiday home rental

Rio Nido house

2 bedrooms / 1 bathroom / sleeps 4

from £199 / night

£1,388 / week

Home rental in Sebastopol

Sebastopol house

2 bedrooms / 2 bathrooms / sleeps 4

1

from £184 / night

£1,128 / week

Holiday home in Monte Rio

Monte Rio house

4 bedrooms / 2 bathrooms / sleeps 8

from £267 / night

£1,601 / week

Lawndale Sonoma County holiday home rental

Lawndale Sonoma County house

3 bedrooms / 2 bathrooms / sleeps 6

from £234 / night

£1,638 / week

Healdsburg holiday home rental

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 8

from £1,128 / night

£5,637 / week

Holiday cottage in Sebastopol

Sebastopol cottage

1 bedroom / 1 bathroom / sleeps 3

5

from £165 / night

£893 - £1,057 / week

Beach hut rental in Geyserville

Geyserville beach hut

1 bedroom / 1 bathroom / sleeps 6

from £118 / night

£824 / week

Viewing 40 of 270
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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