Holiday rentals near Healdsburg Plaza
We found 359 holiday rentals — enter your dates for availability
Find the perfect private holiday rental that's close to Healdsburg Plaza. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a fireplace. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Healdsburg Plaza
Showing deals for:17 Oct - 24 Oct
Image gallery for Modern Retreat - Spectacular View Home Above Dry Creek Valley
9.49.4 out of 10 rating
Exceptional
(19 reviews)
Modern Retreat - Spectacular View Home Above Dry Creek Valley
Healdsburg, CA
8% off
Price is AU$17,728
AU$17,728
AU$2,533 per night
includes taxes & fees
Image gallery for Private 3 Bed + Cottage Wine Country Estate With Pool And More
9.89.8 out of 10 rating
Exceptional
(43 reviews)
Private 3 Bed + Cottage Wine Country Estate With Pool And More
Healdsburg, CA
8% off
Price is AU$14,005
AU$14,005
AU$2,001 per night
includes taxes & fees
Image gallery for Family-Friendly Dry Creek Valley Retreat w/Amazing Views <15 Minutes To Square
1010 out of 10 rating
Exceptional
(13 reviews)
Family-Friendly Dry Creek Valley Retreat w/Amazing Views <15 Minutes To Square
Healdsburg, CA
8% off
Price is AU$10,622
AU$10,622
AU$1,517 per night
includes taxes & fees
Image gallery for Private Wine Country Retreat - Modern Luxury Estate
1010 out of 10 rating
Exceptional
(8 reviews)
Private Wine Country Retreat - Modern Luxury Estate
Healdsburg, CA
7% off
Price is AU$16,939
AU$16,939
AU$2,420 per night
includes taxes & fees
Image gallery for Healdsburg, CA Amazing Resort-like Estate Healdsburg -- 4BD / 3BA
1010 out of 10 rating
Exceptional
(37 reviews)
Healdsburg, CA Amazing Resort-like Estate Healdsburg -- 4BD / 3BA
Windsor, CA
8% off
Price is AU$19,575
AU$19,575
AU$2,796 per night
includes taxes & fees
Image gallery for Stay on the vineyard, hot tub &pool. 5 Queen suites, chef's kitchen, wrap porch
1010 out of 10 rating
Exceptional
(88 reviews)
Stay on the vineyard, hot tub &pool. 5 Queen suites, chef's kitchen, wrap porch
Healdsburg, CA
16% off
Price is AU$13,067
AU$13,067
AU$1,867 per night
includes taxes & fees
Image gallery for 4 BEDROOM plus PRIVATE DEN, 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
1010 out of 10 rating
Exceptional
(191 reviews)
4 BEDROOM plus PRIVATE DEN, 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
Healdsburg, CA
7% off
Price is AU$24,083
AU$24,083
AU$3,440 per night
includes taxes & fees
Image gallery for Dreamy A-Frame Luxury - Privacy - Views-Hot Tub
1010 out of 10 rating
Exceptional
(6 reviews)
Dreamy A-Frame Luxury - Privacy - Views-Hot Tub
Healdsburg, CA
8% off
Price is AU$16,633
AU$16,633
AU$2,376 per night
includes taxes & fees
Image gallery for Healdsburg: Wine Country Retreat-Serenity, Swimming and Solitude
1010 out of 10 rating
Exceptional
(47 reviews)
Healdsburg: Wine Country Retreat-Serenity, Swimming and Solitude
Windsor, CA
8% off
Price is AU$6,892
AU$6,892
AU$985 per night
includes taxes & fees
Image gallery for Wine Country Get Away
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Wine Country Get Away
Windsor, CA
7% off
Price is AU$2,259
AU$2,259
AU$323 per night
includes taxes & fees
Image gallery for Secluded Healdsburg Sanctuary on 10 Private Acres with Vineyard
1010 out of 10 rating
Exceptional
(43 reviews)
Secluded Healdsburg Sanctuary on 10 Private Acres with Vineyard
Healdsburg, CA
16% off
Price is AU$9,908
AU$9,908
AU$1,415 per night
includes taxes & fees
Image gallery for Dry Creek Ranch ~ Pool, HotTub, & Game Barn!
1010 out of 10 rating
Exceptional
(25 reviews)
Dry Creek Ranch ~ Pool, HotTub, & Game Barn!
Healdsburg, CA
11% off
Price is AU$14,831
AU$14,831
AU$2,119 per night
includes taxes & fees
Image gallery for Beautiful Mountain Top Retreat (MTR) less than 10 mins from downtown Healdsburg!
9.89.8 out of 10 rating
Exceptional
(113 reviews)
Beautiful Mountain Top Retreat (MTR) less than 10 mins from downtown Healdsburg!
Healdsburg, CA
8% off
Price is AU$4,643
AU$4,643
AU$663 per night
includes taxes & fees
Image gallery for Beautiful Studio Getaway in the Heart of Wine Country
1010 out of 10 rating
Exceptional
(85 reviews)
Beautiful Studio Getaway in the Heart of Wine Country
Healdsburg, CA
8% off
Price is AU$3,811
AU$3,811
AU$544 per night
includes taxes & fees
Image gallery for Secluded Russian River Farmhouse: Vinyard Retreat, minutes from Healdsburg
9.89.8 out of 10 rating
Exceptional
(46 reviews)
Secluded Russian River Farmhouse: Vinyard Retreat, minutes from Healdsburg
Geyserville, CA
10% off
Price is AU$6,443
AU$6,443
AU$920 per night
includes taxes & fees
Image gallery for Perfect getaway! Riverside pool, river access, 5 min from Healdsburg square!
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Perfect getaway! Riverside pool, river access, 5 min from Healdsburg square!
Healdsburg, CA
9% off
Price is AU$5,251
AU$5,251
AU$750 per night
includes taxes & fees
Image gallery for Gourmet Kitchen in Wine Country w/Hot Tub + Office
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Gourmet Kitchen in Wine Country w/Hot Tub + Office
Windsor, CA
8% off
Price is AU$12,042
AU$12,042
AU$1,720 per night
includes taxes & fees
Image gallery for Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!
1010 out of 10 rating
Exceptional
(85 reviews)
Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!
Geyserville, CA
8% off
Price is AU$9,054
AU$9,054
AU$1,293 per night
includes taxes & fees
Image gallery for Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
1010 out of 10 rating
Exceptional
(62 reviews)
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
Healdsburg, CA
12% off
Price is AU$3,507
AU$3,507
AU$501 per night
includes taxes & fees
Image gallery for Sapphire Canyon Vineyard Guest House
1010 out of 10 rating
Exceptional
(150 reviews)
Sapphire Canyon Vineyard Guest House
Geyserville, CA
8% off
Price is AU$3,466
AU$3,466
AU$495 per night
includes taxes & fees
Image gallery for Minutes to Dozens of World Class Wineries - 2 Bedroom / 2 Bath - Sleeps 6
9.09.0 out of 10 rating
Wonderful
(11 reviews)
Minutes to Dozens of World Class Wineries - 2 Bedroom / 2 Bath - Sleeps 6
Windsor, CA
7% off
Price is AU$3,306
AU$3,306
AU$472 per night
includes taxes & fees
Image gallery for Stay surrounded by Fitch Mountain Park and Open Space Preserve.
9.49.4 out of 10 rating
Exceptional
(24 reviews)
Stay surrounded by Fitch Mountain Park and Open Space Preserve.
Healdsburg, CA
8% off
Price is AU$4,988
AU$4,988
AU$713 per night
includes taxes & fees
Image gallery for Treat Yourself to a Great Getaway
9.69.6 out of 10 rating
Exceptional
(54 reviews)
Treat Yourself to a Great Getaway
Windsor, CA
7% off
Price is AU$3,306
AU$3,306
AU$472 per night
includes taxes & fees
Image gallery for Sonoma County/Wine Country 2 Bed 2 Bath Condominium Resort
9.69.6 out of 10 rating
Exceptional
(121 reviews)
Sonoma County/Wine Country 2 Bed 2 Bath Condominium Resort
Windsor, CA
7% off
Price is AU$2,453
AU$2,453
AU$350 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Healdsburg Plaza
Vineyard View Retreat 8 Minutes to Healdsburg
Sleeps 8 · 4 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
Beautiful Spacious ArtHaus!
Sleeps 12 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Cypress House & Studio, Walk to Healdsburg Plaza by RedAwning
Sleeps 8 · 2 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Private Wine Country Retreat - Modern Luxury Estate
Sleeps 8 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Right in the heart of Healdsburg lies this charming two-bedroom house
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value