Over 1,000 homes

Home in Healdsburg
Chic Wine Country Stay - Walk to River & Downtown
2 beds
Nov. 14 – 19
$499 CAD per night
Superhost
Vacation home in Healdsburg
Downtown Healdsburg Nest
2 beds
Dec. 11 – 16
$575 CAD per night
Superhost
Guesthouse in Healdsburg
Healdsburg Roost in city center
1 queen bed
Oct. 23 – 28
$419 CAD per night
Superhost
Guesthouse in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 queen bed
Dec. 6 – 11
$361 CAD per night
Superhost
Cottage in Healdsburg
Luxurious, Private, Healdsburg Guest House
1 king bed
Oct. 16 – 21
$699 CAD per night
Superhost
Guesthouse in Healdsburg
Healdsburg Cottage-Workspace, Walk to Plaza
1 queen bed
Nov. 13 – 18
$520 CAD per night, originally $589 CAD
Superhost
Guest suite in Healdsburg
Stay on Pony Ranch Vineyard Estate
1 queen bed
Oct. 31 – Nov. 7
$292 CAD per night, originally $331 CAD
Superhost
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 beds
Oct. 24 – 29
$1,044 CAD per night
Superhost
Home in Healdsburg
Healdsburg Garden House
3 beds
Oct. 30 – Nov. 4
$431 CAD per night
Superhost
Guesthouse in Healdsburg
Luxe Guest Suite in Dry Creek 5 mins From Town!
1 king bed
Nov. 14 – 19
$813 CAD per night
Superhost
Guesthouse in Healdsburg
2 BR Guesthouse with private yard in Healdsburg!
2 beds
Oct. 9 – 14
$458 CAD per night
Superhost
Villa in Healdsburg
Hilltop Vista Villa
2 king beds
Oct. 23 – 28
$735 CAD per night
Superhost
Guesthouse in Healdsburg
Healdsburg Contemporary Cottage With Lush Backyard Patio
1 queen bed
Oct. 8 – 13
$1,275 CAD per night
Plus
Loft in Healdsburg
The laundry room
1 king bed
Oct. 6 – 13
$364 CAD per night, originally $431 CAD
Superhost
Cottage in Healdsburg
Bee Haven Cottage
1 queen bed
Dec. 29 – Jan. 3
$570 CAD per night
Superhost
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
5 beds
Nov. 10 – 15
$2,956 CAD per night
Superhost
Home in Healdsburg
Vineyard Modern Barn House - Dry Creek Valley
2 king beds
Nov. 13 – 20
$755 CAD per night, originally $817 CAD
Superhost
Home in Healdsburg
Healdsburg Homestead
4 beds
Oct. 9 – 14
$1,372 CAD per night
Superhost
Home in Healdsburg
Wine Country Cottage in Healdsburg
1 queen bed
Nov. 6 – 11
$334 CAD per night
Superhost
Cottage in Healdsburg
Modern, Secluded Retreat - Walk to the Plaza!
3 king beds
Dec. 1 – 6
$1,158 CAD per night
Superhost
Home in Healdsburg
Dry Creek w/Hot Tub, Bocce, Vineyard Views
3 beds
Nov. 28 – Dec. 5
$743 CAD per night, originally $805 CAD
Superhost
Home in Healdsburg
Wine Country Cottage Walkable to River or Downtown
2 beds
Nov. 28 – Dec. 3
$515 CAD per night
Superhost
Vacation home in Healdsburg
Downtown Healdsburg Hideaway
2 beds
Nov. 8 – 13
$771 CAD per night
Superhost
Apartment in Healdsburg
Modern Studio in Downtown Healdsburg
1 queen bed
Mar. 12 – 17
$464 CAD per night
Superhost