Holiday rentals near Healdsburg Plaza
We found 361 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:7 Nov - 14 Nov
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 S$15,763
S$15,763
S$2,252 per night
includes taxes & fees
Image gallery for Private 1-bedroom Guest House with Great Amenities
1010 out of 10 rating
Exceptional
(11 reviews)
Private 1-bedroom Guest House with Great Amenities
Healdsburg, CA
8% off
Price is S$5,258
S$5,258
S$751 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 S$9,291
S$9,291
S$1,327 per night
includes taxes & fees
Image gallery for Hidden Pocket: Private Sonoma Wine Country Retreat
1010 out of 10 rating
Exceptional
(102 reviews)
Hidden Pocket: Private Sonoma Wine Country Retreat
Healdsburg, CA
8% off
Price is S$10,454
S$10,454
S$1,493 per night
includes taxes & fees
Image gallery for 10 min to Healdsburg - Modern Farmhouse with Pool, Spa & Views
1010 out of 10 rating
Exceptional
(9 reviews)
10 min to Healdsburg - Modern Farmhouse with Pool, Spa & Views
Windsor, CA
6% off
Price is S$11,818
S$11,818
S$1,688 per night
includes taxes & fees
Image gallery for Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza
1010 out of 10 rating
Exceptional
(169 reviews)
Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza
Healdsburg, CA
16% off
Price is S$8,193
S$8,193
S$1,170 per night
includes taxes & fees
Image gallery for Luxury Home in Healdsburg with a Private Pool plus complimentary wine tastings.
1010 out of 10 rating
Exceptional
(49 reviews)
Luxury Home in Healdsburg with a Private Pool plus complimentary wine tastings.
Geyserville, CA
8% off
Price is S$12,854
S$12,854
S$1,836 per night
includes taxes & fees
Image gallery for Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg
1010 out of 10 rating
Exceptional
(34 reviews)
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg
Healdsburg, CA
8% off
Price is S$11,355
S$11,355
S$1,622 per night
includes taxes & fees
Image gallery for Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!
9.69.6 out of 10 rating
Exceptional
(168 reviews)
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!
Healdsburg, CA
8% off
Price is S$4,943
S$4,943
S$706 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
15% off
Price is S$2,200
S$2,200
S$314 per night
includes taxes & fees
Image gallery for Healdsburg Hilltop Retreat :: Craftsman detail, modern comforts & stunning VIEWS
9.89.8 out of 10 rating
Exceptional
(154 reviews)
Healdsburg Hilltop Retreat :: Craftsman detail, modern comforts & stunning VIEWS
Healdsburg, CA
12% off
Price is S$2,737
S$2,737
S$391 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 S$15,122
S$15,122
S$2,160 per night
includes taxes & fees
Image gallery for Modern Vineyard Farmhouse - Close to Downtown Healdsburg - 4 BD/4 Ensuite Baths
1010 out of 10 rating
Exceptional
(8 reviews)
Modern Vineyard Farmhouse - Close to Downtown Healdsburg - 4 BD/4 Ensuite Baths
Healdsburg, CA
8% off
Price is S$13,284
S$13,284
S$1,898 per night
includes taxes & fees
Image gallery for Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
9.69.6 out of 10 rating
Exceptional
(181 reviews)
Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
Windsor, CA
14% off
Price is S$6,626
S$6,626
S$947 per night
includes taxes & fees
Image gallery for Alexander Valley Modern Farmhouse with Vintage Charm - Newly Renovated pool
1010 out of 10 rating
Exceptional
(41 reviews)
Alexander Valley Modern Farmhouse with Vintage Charm - Newly Renovated pool
Healdsburg, CA
12% off
Price is S$12,775
S$12,775
S$1,825 per night
includes taxes & fees
Image gallery for Secluded Healdsburg Sanctuary on 10 Private Acres with Vineyard
1010 out of 10 rating
Exceptional
(44 reviews)
Secluded Healdsburg Sanctuary on 10 Private Acres with Vineyard
Healdsburg, CA
16% off
Price is S$8,588
S$8,588
S$1,227 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 S$3,901
S$3,901
S$557 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 S$3,200
S$3,200
S$457 per night
includes taxes & fees
Image gallery for Heart of Wine Country, Cute Cottage w/Hot Tub
9.49.4 out of 10 rating
Exceptional
(27 reviews)
Heart of Wine Country, Cute Cottage w/Hot Tub
Windsor, CA
8% off
Price is S$3,956
S$3,956
S$565 per night
includes taxes & fees
Image gallery for Updated 5 BR house w/ hot tub - 5 min walk to downtown!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Updated 5 BR house w/ hot tub - 5 min walk to downtown!
Geyserville, CA
6% off
Price is S$9,163
S$9,163
S$1,309 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 S$5,410
S$5,410
S$773 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
(28 reviews)
Perfect getaway! Riverside pool, river access, 5 min from Healdsburg square!
Healdsburg, CA
9% off
Price is S$4,647
S$4,647
S$664 per night
includes taxes & fees
Image gallery for Historic Queen Anne Victorian in the Heart of Windsor
1010 out of 10 rating
Exceptional
(21 reviews)
Historic Queen Anne Victorian in the Heart of Windsor
Windsor, CA
8% off
Price is S$4,286
S$4,286
S$612 per night
includes taxes & fees
Image gallery for The Roost - Garden Studio
1010 out of 10 rating
Exceptional
(16 reviews)
The Roost - Garden Studio
Healdsburg, CA
18% off
Price is S$3,213
S$3,213
S$459 per night
includes taxes & fees
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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
34 reviews(34 reviews)
Beautiful Spacious ArtHaus!
Sleeps 12 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
26 reviews(26 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)
Dreamy A-Frame Luxury - Privacy - Views-Hot Tub
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Private Wine Country Retreat - Modern Luxury Estate
Sleeps 8 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
8 reviews(8 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