Vacation rentals in Healdsburg

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Top-rated vacation rentals in Healdsburg

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile in Healdsburg includes equipped kitchen. Pick up breakfast needs before arriving. House truth: Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. It can be disruptive to sleep (or not, some say it isn't a bother). LOFT AVAILABLE BUT TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. TOT #3294N
Nov. 3 – 10
$467 CAD per night
4.97 out of 5 average rating, 465 reviews
Guest favourite
Home in Healdsburg
Wine Country Cottage Walkable to River or Downtown
Centrally located retreat 5 blocks from downtown, Russian River and 3 blocks from at least 9 wineries. Living room fully opens to private deck w/BBQ, outdoor kitchen, dining space and fire place Gourmet equipped kitchen with many cooking amenities to enjoy wine and a great meal in the garden patio or BBQ outside and relax by the fire Luxury bathroom with heated towel rack and bidet Two bedrooms with one converting into a home office. Lots of extra amenities and thoughtful comfortable touches
Dec. 9 – 16
$366 CAD per night
4.96 out of 5 average rating, 144 reviews
Guest favourite
Home in Healdsburg
Vineyard Modern Barn House - Dry Creek Valley
Stylish house on a 9 acre vineyard. Beautifully crafted, the property features high end furnishings, professionally laundered/ironed sheets, original art, and 2 master bedroom suites separated by a great room w/full kitchen. Close-in location up a gated road, 5 min. to the Plaza. Amazing view from the 45 foot covered porch overlooking vineyards and Dry Creek Valley. Perfect for two couples; not suitable for infants or children under 8, max 2 daytime guests. No parties or pets allowed.
Nov. 13 – 20
$746 CAD per night
4.98 out of 5 average rating, 391 reviews

Popular amenities for Healdsburg vacation rentals

Stay near Healdsburg's top sights

Healdsburg Plaza47 locals recommend
Healdsburg Veterans Memorial Beach5 locals recommend
Bravas Bar de Tapas68 locals recommend
Willi's | Seafood & Raw Bar76 locals recommend
Big John's Market43 locals recommend
Safeway27 locals recommend

Other great vacation rentals in Healdsburg

Guest favourite
Guesthouse in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
Aug. 7 – 14
$297 CAD per night
4.98 out of 5 average rating, 245 reviews
Guest favourite
Guesthouse in Healdsburg
Healdsburg Contemporary Cottage With Lush Backyard Patio
Jul. 12 – 19
$1,061 CAD per night
4.98 out of 5 average rating, 174 reviews
Guest favourite
Home in Healdsburg
Modern Wine Country Home on 10 acres with vineyard
Sep. 27 – Oct. 4
$1,180 CAD per night
4.97 out of 5 average rating, 147 reviews
Guest favourite
Home in Healdsburg
Dry Creek w/Hot Tub, Bocce, Vineyard Views
Nov. 26 – Dec. 3
$741 CAD per night
4.91 out of 5 average rating, 122 reviews
Guest favourite
Guesthouse in Healdsburg
Healdsburg Cottage-Workspace, Walk to Plaza
May 8 – 15
$519 CAD per night
4.93 out of 5 average rating, 296 reviews
Guest favourite
Cottage in Healdsburg
Bee Haven Cottage
Apr. 25 – May 2
$460 CAD per night
5.0 out of 5 average rating, 156 reviews
Guest favourite
Home in Healdsburg
Dry Creek Valley Cottage
Jul. 20 – 27
$303 CAD per night
4.96 out of 5 average rating, 426 reviews
Superhost
Home in Healdsburg
C - Wineries/breweries seconds away
Apr. 17 – 24
$244 CAD per night
4.82 out of 5 average rating, 414 reviews
Guest favourite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
Apr. 5 – 12
$810 CAD per night
4.95 out of 5 average rating, 104 reviews
Guest favourite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
May 16 – 23
$310 CAD per night
4.92 out of 5 average rating, 407 reviews
Superhost
Home in Healdsburg
Modern Home in Hburg Wine Country
Sep. 28 – Oct. 5
$969 CAD per night
4.88 out of 5 average rating, 138 reviews
Guest favourite
Home in Healdsburg
10 Acre Vineyard Stay w/Hot Tub + Bocce Court
Dec. 3 – 10
$534 CAD per night
5.0 out of 5 average rating, 42 reviews

Quick stats about vacation rentals in Healdsburg

Total rentals

100 properties

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

70 properties are a good fit for families

Total number of reviews

4.1K reviews

Nightly prices starting at

$108 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Healdsburg