Chianti holiday rentals

From simple studios to luxe lofts, find holiday rentals that are right for you on Airbnb.

Holiday rentals in Chianti

$203 NZD Dry Creek Valley Cottage
209 reviews

Enjoy your stay in beautiful Dry Creek Valley, a pastoral rural setting surrounded by vineyards and local wineries, minutes from Healdsburg's historic quaint downtown plaza. T... read more
$231 NZD Stay on a Vineyard Estate
86 reviews

Brand new Guest House with private entrance on gated Vineyard Estate. Overlooks pool and vineyards with views to Mount St. Helena. Gas fireplace, refrigerator, microwave, Keur... read more
$189 NZD The Little House on the Hill
152 reviews

The Little House is a studio cottage with kitchen, bathroom, queen bed, wifi, sitting/dining area with TV for movies and Apple TV. Wine, coffee, light snacks and a fine view com... read more
$350 NZD The Cabin HBG
49 reviews

This scenic cabin rental is located 2 miles from the historic Healdsburg Plaza on Fitch Mountain. Set under majestic oak trees, on a quiet private country lane, this rental has ... read more
$352 NZD Healdsburg Roost in city center
40 reviews

The Roost is a licensed guest room that is located 2 blocks from the central plaza of Healdsburg in a quiet residential neighborhood. The Roost occupies a corner of an historic... read more
$329 NZD Northern Alexander Valley 2Bd Cottage
3 reviews

Heron Hill Cottage is a 2 bedroom home minutes from the charming town of Cloverdale. Our end of the lane privacy invites you for a restful stay in this beautiful northern Sonoma... read more

Favourite Chianti holiday rentals

$223 NZD Heaven in the Oaks pure luxury B&B
298 reviews

An attractive, ultra-romantic, almost-a-cottage Bed&Breakfast is waiting for you in our restored 1930s-era vacation home in celebrated Healdsburg We consider our B&B as a destin... read more
$126 NZD Cobb Tree House
7 reviews

Our cabin is within one mile of downtown Cobb. It is a lovely walk or a short drive. There is a pizza place, pub, a coffee shop with wifi, a grocery store, post office, golf, an... read more
$175 NZD Guest Suite on Vineyard for 2
112 reviews

Sweet Suite in our mountain top home/working winery. Use of pool and hot tub (suspended December-March) , multiple sitting areas and views to die for. Full breakfast served. IF... read more
2 reviews

For fun times or quiet times, the cottage is near famed wine bars, vineyards, fine fare, art galleries and boutique shopping. On Fitch Mountain, 5 minutes from Healdsburg ~ home... read more
$265 NZD Stay upstairs in our small winery
110 reviews

Unique wine country getaway. Two adjacent bedrooms both with queen beds located upstairs above Winery. Bath is downstairs. Winery building is private during your stay. (tastings... read more
$161 NZD Ride, Wine and Dine
96 reviews

We have a beautiful home on a quiet street, the master bedroom with a private on- suite is included in the pictures. Come taste the bounty of the Alexander award winning wines. ... read more

More holiday rentals in Chianti

$554 NZD Vineyard Estate Cottage / Poolhouse
7 reviews

Surrounded by vineyards, this dog-friendly cottage provides a secluded and very scenic wine country experience. You will enjoy total privacy in our custom-built cottage overlook... read more
$516 NZD Contemporary, brand-new Retreat
8 reviews

Internationally acclaimed artist/owner designed ArtShed to pamper your creativity. On a country lane under the oaks, this new house in the heart of Dry Creek Valley is only five... read more
$175 NZD Cloverdale Retreat
21 reviews

My place is close to the beach, nightlife, and the airport. You’ll love my place because of the location, the people, and the ambiance. Private Bedroom and private bath with sho... read more
$336 NZD Healdsburg Cottage-Walk to Plaza
74 reviews

This light-filled cottage is a comfortable hide-away in a friendly, historic neighborhood just 5 blocks from the Healdsburg Plaza. Dine or have a glass of wine in the private g... read more
$559 NZD Alexander Valley Estate in the Vineyards
1 review

Buy 6 nights and get the 7th for free! At this charming, historic 3BR/2BA home next door to Starlite Vineyards, a private tour and tasting come with your stay. Enjoy space, co... read more
$561 NZD Healdsburg Downtown Cottage-2 bedroom/1 bathroom
1 review

This home is only 2 blocks from the Healdsburg Square. It's surprisingly private and quiet in the house for being downtown. Bosch washer/dryer and recently remodeled bathroom. C... read more

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