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

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8 Holiday homes

Windsor holiday cottage rental

Windsor cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £137 / night

£957 / week

1 / 15

Holiday home in Windsor

Windsor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £151 / night

£1,052 / week

1 / 4

Holiday home in Windsor

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £193 / night

£1,355 - £1,752 / week

1 / 30

Holiday home in Windsor

Windsor house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £113 / night

£788 - £1,865 / week

1 / 22

Holiday home with indoor pool in Windsor

Windsor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £529 / night

£2,913 / week

1 / 49

Holiday condo with golf nearby in Windsor

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £456 / night

£3,188 / week

1 / 4

Holiday home in Windsor

Windsor house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £105 / night

£732 - £1,694 / week

1 / 27

Windsor holiday home rental

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £296 / night

£1,822 / week

1 / 11

Great rentals within 20 miles that match your search

Bodega Bay holiday home rental

Bodega Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from £866 / night

£6,056 / week

1 / 15

Guerneville holiday home rental

Guerneville house

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 28

from £1,453 / night

£8,716 / week

1 / 41

Home rental in Forestville

Forestville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £451 / night

£2,323 - £3,068 / week

1 / 37

Healdsburg holiday home rental

Healdsburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £592 / night

£3,415 / week

1 / 36

Holiday home in Kenwood

Kenwood house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £451 / night

£3,187 / week

1 / 23

Home rental in St. Helena with golf nearby

St. Helena house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £638 / night

£3,643 / week

1 / 18

Holiday home in Forestville

Forestville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £204 / night

£1,162 / week

1 / 13

Holiday home in Santa Rosa

Santa Rosa house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £381 / night

£2,398 / week

1 / 24

Holiday farmhouse in Forestville

Forestville farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £274 / night

£1,913 / week

1 / 24

Studio rental in Santa Rosa

Santa Rosa studio

  • Studio
  • 1 bathroom
  • sleeps 3

from £173 / night

£1,102 / week

1 / 12

Holiday home in St. Helena

St. Helena house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £228 / night

£1,708 / week

1 / 11

Holiday cottage in Petaluma

Petaluma cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £137 / night

£820 / week

1 / 15

Holiday home in Healdsburg

Healdsburg house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

from £2,641 / night

£15,482 / week

1 / 95

Holiday home in Healdsburg

Healdsburg house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £820 / night

£4,554 / week

1 / 40

Monte Rio holiday home rental

Monte Rio house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

from £205 / night

£1,002 - £1,640 / week

1 / 13

Holiday home in Bodega Bay

Bodega Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £724 / night

£5,068 / week

1 / 26

Cazadero holiday log cabin rental

Cazadero log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £105 / night

£733 / week

1 / 33

Monte Rio holiday home accommodation

Monte Rio house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £251 / night

£1,753 / week

1 / 28

Holiday home with swimming pool in St. Helena

St. Helena house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 12

from £5,464 / night

£38,249 / week

1 / 22

Kenwood holiday home rental

Kenwood house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £3,188 / night

£22,312 / week

1 / 17

Healdsburg holiday home accommodation

Healdsburg house

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 8

from £167 / night

£1,169 / week

1 / 44

Holiday home rental

Monte Rio house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £151 / night

£943 / week

1 / 15

Home rental in Forestville

Forestville house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £274 / night

£1,913 / week

1 / 42

Home rental in Kenwood

Kenwood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £305 / night

£2,232 - £2,550 / week

1 / 24

Holiday home in Healdsburg

Healdsburg house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £820 / night

£5,738 / week

1 / 20

Holiday home in Forestville

Forestville house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £1,002 / night

£4,554 / week

1 / 11

Holiday cottage in Healdsburg

Healdsburg cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £228 / night

£1,594 / week

1 / 6

Holiday home rental

Duncans Mills house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £351 / night

£2,455 / week

1 / 21

Kenwood holiday villa rental

Kenwood villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £1,594 / night

£11,156 / week

1 / 17

Healdsburg holiday home rental

Healdsburg house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,275 / night

£7,650 / week

1 / 23

Holiday home in Kenwood

Kenwood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £343 / night

£2,160 / week

1 / 25

Holiday home in Bodega Bay

Bodega Bay house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £542 / night

£3,793 / week

1 / 62

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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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