Holiday rentals near Chalk Hill Estate Vineyard
We found 1,516 holiday rentals — enter your dates for availability
Select the perfect holiday rental within close proximity to Chalk Hill Estate Vineyard. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as air conditioning and cable TV. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Chalk Hill Estate Vineyard
Showing deals for:14 Nov - 21 Nov
Image gallery for Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
1010 out of 10 rating
Exceptional
(63 reviews)
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Healdsburg, CA
13% off
Price is AU$20,960
AU$20,960
AU$2,994 per night
includes taxes & fees
Image gallery for Sunny Poolside Winecountry Retreat
1010 out of 10 rating
Exceptional
(136 reviews)
Sunny Poolside Winecountry Retreat
Guerneville, CA
8% off
Price is AU$5,602
AU$5,602
AU$800 per night
includes taxes & fees
Image gallery for Secluded Russian River retreat: nature & privacy in pastoral Duncans Mills.
1010 out of 10 rating
Exceptional
(35 reviews)
Secluded Russian River retreat: nature & privacy in pastoral Duncans Mills.
Duncans Mills, CA
11% off
Price is AU$2,881
AU$2,881
AU$412 per night
includes taxes & fees
Image gallery for Pool Paradise in Wine Country!
1010 out of 10 rating
Exceptional
(14 reviews)
Pool Paradise in Wine Country!
Kenwood, CA
8% off
Price is AU$8,263
AU$8,263
AU$1,180 per night
includes taxes & fees
Image gallery for Large Country Estate in Downtown Sebastopol
1010 out of 10 rating
Exceptional
(10 reviews)
Large Country Estate in Downtown Sebastopol
Sebastopol, CA
8% off
Price is AU$6,445
AU$6,445
AU$921 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 AU$2,549
AU$2,549
AU$364 per night
includes taxes & fees
Image gallery for Gated and private mountaintop 30-acre Vineyard Estate, Pool, Jacuzzi, Gardens
1010 out of 10 rating
Exceptional
(61 reviews)
Gated and private mountaintop 30-acre Vineyard Estate, Pool, Jacuzzi, Gardens
St. Helena, CA
19% off
Price is AU$18,393
AU$18,393
AU$2,628 per night
includes taxes & fees
Image gallery for Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8
1010 out of 10 rating
Exceptional
(23 reviews)
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8
Santa Rosa, CA
8% off
Price is AU$14,793
AU$14,793
AU$2,113 per night
includes taxes & fees
Image gallery for 𝑳𝒖𝒙𝒖𝒓𝒚 𝑷𝒓𝒊𝒗𝒂𝒕𝒆 𝑬𝒔𝒕𝒂𝒕𝒆 𝒂𝒕 𝒁𝒐𝒆𝒍𝒍𝒂 𝑽𝒊𝒏𝒆𝒚𝒂𝒓𝒅.𝑷𝑶𝑶𝑳&𝑺𝑷𝑨!𝑮𝑨𝑴𝑬𝑹𝑶𝑶𝑴!
9.69.6 out of 10 rating
Exceptional
(62 reviews)
𝑳𝒖𝒙𝒖𝒓𝒚 𝑷𝒓𝒊𝒗𝒂𝒕𝒆 𝑬𝒔𝒕𝒂𝒕𝒆 𝒂𝒕 𝒁𝒐𝒆𝒍𝒍𝒂 𝑽𝒊𝒏𝒆𝒚𝒂𝒓𝒅.𝑷𝑶𝑶𝑳&𝑺𝑷𝑨!𝑮𝑨𝑴𝑬𝑹𝑶𝑶𝑴!
Healdsburg, CA
20% off
Price is AU$17,426
AU$17,426
AU$2,489 per night
includes taxes & fees
Image gallery for Happy House Getaway – Pool, Hot Tub & Chef’s Kitchen in Wine Country
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Happy House Getaway – Pool, Hot Tub & Chef’s Kitchen in Wine Country
Santa Rosa, CA
28% off
Price is AU$4,027
AU$4,027
AU$575 per night
includes taxes & fees
Image gallery for Historic Saint Helena farm house one block from Main Street
1010 out of 10 rating
Exceptional
(211 reviews)
Historic Saint Helena farm house one block from Main Street
St. Helena, CA
12% off
Price is AU$16,484
AU$16,484
AU$2,355 per night
includes taxes & fees
Image gallery for Modern Home in downtown Middletown! Walk to shops & restaurants!
9.89.8 out of 10 rating
Exceptional
(45 reviews)
Modern Home in downtown Middletown! Walk to shops & restaurants!
Middletown, CA
8% off
Price is AU$2,455
AU$2,455
AU$351 per night
includes taxes & fees
Image gallery for Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019
9.89.8 out of 10 rating
Exceptional
(90 reviews)
Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL23-019
St. Helena, CA
14% off
Price is AU$11,646
AU$11,646
AU$1,664 per night
includes taxes & fees
Image gallery for Home near montgomery village w/ heated pool
9.69.6 out of 10 rating
Exceptional
(44 reviews)
Home near montgomery village w/ heated pool
Santa Rosa, CA
8% off
Price is AU$5,755
AU$5,755
AU$822 per night
includes taxes & fees
Image gallery for 'Moonview Ranch' on 20 Acres in Sonoma County!
9.69.6 out of 10 rating
Exceptional
(34 reviews)
'Moonview Ranch' on 20 Acres in Sonoma County!
Sebastopol, CA
7% off
Price is AU$2,410
AU$2,410
AU$344 per night
includes taxes & fees
Image gallery for Glen Ellen Estate - Pool, Hot Tub on 2 acres
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Glen Ellen Estate - Pool, Hot Tub on 2 acres
Glen Ellen, CA
8% off
Price is AU$9,781
AU$9,781
AU$1,397 per night
includes taxes & fees
Image gallery for Wine Country Hideaway: 4BR, 2200Sf Home With Swimming Pool and Pickleball area
1010 out of 10 rating
Exceptional
(83 reviews)
Wine Country Hideaway: 4BR, 2200Sf Home With Swimming Pool and Pickleball area
Forestville, CA
8% off
Price is AU$10,535
AU$10,535
AU$1,505 per night
includes taxes & fees
Image gallery for Sonoma Valley Vacation Home
9.69.6 out of 10 rating
Exceptional
(43 reviews)
Sonoma Valley Vacation Home
Santa Rosa, CA
8% off
Price is AU$4,260
AU$4,260
AU$609 per night
includes taxes & fees
Image gallery for Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills
9.29.2 out of 10 rating
Wonderful
(17 reviews)
Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills
Duncans Mills, CA
8% off
Price is AU$2,561
AU$2,561
AU$366 per night
includes taxes & fees
Image gallery for Sunny View Cottage in the Beautiful Wine Country
1010 out of 10 rating
Exceptional
(273 reviews)
Sunny View Cottage in the Beautiful Wine Country
Santa Rosa, CA
8% off
Price is AU$2,544
AU$2,544
AU$363 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
(170 reviews)
Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza
Healdsburg, CA
11% off
Price is AU$10,203
AU$10,203
AU$1,458 per night
includes taxes & fees
Image gallery for Home near Calistoga w/ heated pool & hot tub
9.29.2 out of 10 rating
Wonderful
(32 reviews)
Home near Calistoga w/ heated pool & hot tub
Santa Rosa, CA
8% off
Price is AU$5,888
AU$5,888
AU$841 per night
includes taxes & fees
Image gallery for Private Hilltop Vineyard Views! Luxury Home 6 Acres with private Pool & Hot Tub
1010 out of 10 rating
Exceptional
(124 reviews)
Private Hilltop Vineyard Views! Luxury Home 6 Acres with private Pool & Hot Tub
Glen Ellen, CA
16% off
Price is AU$16,192
AU$16,192
AU$2,313 per night
includes taxes & fees
Image gallery for Fully Remodeled Private Wine Country Bungalow! Sunny Treetop Views, Luxury Beds
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Fully Remodeled Private Wine Country Bungalow! Sunny Treetop Views, Luxury Beds
Forestville, CA
8% off
Price is AU$4,965
AU$4,965
AU$709 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chalk Hill Estate Vineyard
Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)
Sleeps 12 · 6 bedrooms · 4+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
39 reviews(39 reviews)
Wine Country Estate Home
Sleeps 8 · 4 bedrooms · 4+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
5 reviews(5 reviews)
Serene wine country home, central AC, close to golf, hiking, wineries & dining
Sleeps 12 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Calistoga Wine Ranch
Sleeps 14 · 6 bedrooms · 6 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Designer's Ranch-Style Farm Stay Get-Away
Sleeps 12 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
✨River View Lodge | Tasting at Croix included!
Sleeps 8 · 3 bedrooms · 1+ bathroom
9.69.6 out of 10
Exceptionalexceptional
70 reviews(70 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