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Cottages in Healdsburg and Cabins - Holiday Lettings - Holiday Rentals Healdsburg

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75 Holiday homes

Holiday villa in Healdsburg

Healdsburg villa

3 bedrooms • 5 bathrooms • sleeps 8

from £649 / night

£4,539 / week

1 / 26

Holiday home with golf nearby in Healdsburg

Healdsburg house

3 bedrooms • 2 bathrooms • sleeps 8

from £356 / night

£2,489 / week

1 / 25

Holiday home with golf nearby in Healdsburg

Healdsburg house

2 bedrooms • 1 bathroom • sleeps 6

from £293 / night

£2,050 / week

1 / 23

Healdsburg holiday home rental

Healdsburg house

4 bedrooms • 7 bathrooms • sleeps 8

from £1,496 / night

£8,725 / week

1 / 10

Holiday villa in Healdsburg

Healdsburg villa

4 bedrooms • 6 bathrooms • sleeps 8

from £1,832 / night

£12,821 / week

1 / 13

Holiday cottage in Healdsburg

Healdsburg cottage

2 bedrooms • 2 bathrooms • sleeps 4

from £209 / night

£1,457 / week

1 / 6

Holiday home in Healdsburg

Healdsburg house

1 bedroom • 1 bathroom • sleeps 4

from £164 / night

£1,293 / week

1 / 5

Holiday cottage with golf nearby in Healdsburg

Healdsburg cottage

2 bedrooms • 1 bathroom • sleeps 6

from £440 / night

£3,075 / week

1 / 16

Holiday home in Healdsburg

Healdsburg house

4 bedrooms • 3 bathrooms • sleeps 8

from £1,335 / night

£9,342 / week

1 / 45

Healdsburg holiday home accommodation

Healdsburg house

3 bedrooms • 6 bathrooms • sleeps 8

from £153 / night

£1,067 / week

1 / 44

Holiday home in Healdsburg

Healdsburg house

3 bedrooms • 2 bathrooms • sleeps 8

from £628 / night

£4,393 / week

1 / 15

Holiday chateau with golf nearby in Healdsburg

Healdsburg chateau

5 bedrooms • 4 bathrooms • sleeps 12

from £1,502 / night

£10,513 / week

1 / 44

Holiday home in Healdsburg

Healdsburg house

2 bedrooms • 2 bathrooms • sleeps 4

from £753 / night

£5,265 / week

1 / 70

Holiday cottage with golf nearby in Healdsburg

Healdsburg cottage

2 bedrooms • 1 bathroom • sleeps 6

from £230 / night

£1,611 / week

1 / 21

Holiday cottage rental

Healdsburg cottage

2 bedrooms • 2 bathrooms • sleeps 6

from £384 / night

£2,689 / week

1 / 26

Holiday home with golf nearby in Healdsburg

Healdsburg house

2 bedrooms • 2 bathrooms • sleeps 4

from £167 / night

£1,166 / week

1 / 40

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

Holiday cottage in Santa Rosa

Santa Rosa cottage

2 bedrooms • 1 bathroom • sleeps 6

from £162 / night

£1,226 - £1,517 / 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 condo with golf nearby in Windsor

Windsor condo

2 bedrooms • 2 bathrooms • sleeps 6

from £417 / night

£2,914 / week

1 / 4

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 home rental

Duncans Mills house

2 bedrooms • 1 bathroom • sleeps 5

from £321 / night

£2,244 / week

1 / 21

Holiday home in Cobb

Cobb house

2 bedrooms • 2 bathrooms • sleeps 8

from £208 / night

£1,083 / week

1 / 8

Holiday home rental

Freestone house

4 bedrooms • 4 bathrooms • sleeps 12

from £583 / night

£4,080 / week

1 / 67

Holiday villa rental

Cazadero villa

4 bedrooms • 4 bathrooms • sleeps 16

from £999 / night

£6,994 / week

1 / 6

Geyserville holiday farmhouse rental

Geyserville farmhouse

3 bedrooms • 2 bathrooms • sleeps 7

from £421 / night

£2,187 / week

1 / 16

Middletown holiday home rental

Middletown house

3 bedrooms • 3 bathrooms • sleeps 10

from £210 / night

£1,466 / week

1 / 21

Holiday home rental

Guerneville house

3 bedrooms • 2 bathrooms • sleeps 9

from £252 / night

£1,759 / week

1 / 17

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 Forestville

Forestville house

2 bedrooms • 1 bathroom • sleeps 4

from £189 / night

£1,074 / week

1 / 13

Windsor holiday home rental

Windsor house

3 bedrooms • 2 bathrooms • sleeps 6

from £274 / night

£1,685 / week

1 / 11

Holiday home in Occidental

Occidental house

2 bedrooms • 2 bathrooms • sleeps 9

from £210 / night

£1,465 / week

1 / 28

Holiday home rental

Monte Rio house

1 bedroom • 1 bathroom • sleeps 4

from £122 / night

£798 / week

1 / 15

Holiday home in Guerneville

Guerneville house

2 bedrooms • 2 bathrooms • sleeps 4

from £440 / night

£3,075 / week

1 / 36

Calistoga holiday home rental

Calistoga house

4 bedrooms • 2 bathrooms • sleeps 8

from £607 / night

£4,246 / week

1 / 21

Holiday home with golf nearby in Santa Rosa

Santa Rosa house

4 bedrooms • 4 bathrooms • sleeps 10

from £217 / night

£1,517 / week

1 / 75

Holiday condo accommodation

Cloverdale condo

1 bedroom • 1 bathroom • sleeps 4

from £126 / night

£670 / week

1 / 7

Holiday villa in Fulton

Fulton villa

4 bedrooms • 3 bathrooms • sleeps 8

from £251 / night

£1,751 / week

1 / 35

Holiday home in Calistoga

Calistoga house

3 bedrooms • 3 bathrooms • sleeps 8

from £670 / night

£4,686 / week

1 / 49

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Healdsburg holidays

Located along the Russian River at the centre of Sonoma County wine country, Healdsburg offers a perfect holiday paradise, especially for wine lovers and outdoor enthusiasts. Every year, visitors come here from all over the world to experience tours through the rolling hillsides covered with vineyards and olive groves. Some of the finest award winning olive oils, wines, and champagnes in the world are produced right here. The mountains lie within easy reach of downtown Healdsburg, offering endless outdoor activities against a backdrop of rugged natural beauty. Stay in your own private holiday rental and enjoy a cup of coffee on your deck as the sun rises. Head into town for shopping, art galleries, craft studios, and seasonal festivals. When you're ready to explore the wilderness, there are miles of scenic trails and picnic areas here offering beautiful overlooks and wildlife spotting opportunities. At night, come home to your holiday rental in Healdsburg. Pool and luxury gourmet kitchens are features that many rentals offer, which can make your private condo or holiday home a great place for relaxing in style or hosting dinner for your family and friends.

Here are a few additional suggestions for your trip:

  • Tour wine country: A vineyard tour is an indispensible part of the Healdsburg Experience.
  • Go biking: Explore the steep back country trails by bicycle or rent a bike and peddle around town and have a freewheeling afternoon on a bicycle wine tour.
  • Take a balloon ride: Experience the majestic beauty of Sonoma from the sky. Take a ride in a colourful balloon at sunrise and follow it up with a romantic champagne brunch.
  • Go boating and fishing: Head out onto Healdsburg's tranquil lakes and waterways for some of the best fly fishing opportunities in the state.
  • Spend an afternoon in the spa: Healdsburg spa venues are truly world class. After a few days of mountain biking and rock climbing, indulge in an afternoon of serious pampering.
  • Go bird watching and wildlife spotting: The Healdsburg area is home to some of California's most elusive bird and wildlife species. Come here to see eagles, hawks, otters, foxes, and black bears.

Sonoma country is becoming increasingly popular for weekend getaways, family reunions, and Healdsburg wedding locations. Bring your friends and family, rent a luxury holiday home or seasonal condo, and let the holiday memories begin.

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