Holiday rentals near Chalk Hill Estate Vineyard
We found 1,502 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:3 Oct - 10 Oct
Image gallery for Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
1010 out of 10 rating
Exceptional
(60 reviews)
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Healdsburg, CA
13% off
Price is AU$20,622
AU$20,622
AU$2,946 per night
includes taxes & fees
Image gallery for True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
1010 out of 10 rating
Exceptional
(11 reviews)
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Healdsburg, CA
8% off
Price is AU$5,285
AU$5,285
AU$755 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$2,281
AU$2,281
AU$326 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 AU$14,916
AU$14,916
AU$2,131 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
(42 reviews)
Modern Home in downtown Middletown! Walk to shops & restaurants!
Middletown, CA
8% off
Price is AU$2,473
AU$2,473
AU$353 per night
includes taxes & fees
Image gallery for Happy House Getaway – Pool, Hot Tub & Chef’s Kitchen in Wine Country
1010 out of 10 rating
Exceptional
(8 reviews)
Happy House Getaway – Pool, Hot Tub & Chef’s Kitchen in Wine Country
Santa Rosa, CA
22% off
Price is AU$5,076
AU$5,076
AU$725 per night
includes taxes & fees
Image gallery for Backyard Oasis, 3/1 Home w/ Hot Tub & Central AC
1010 out of 10 rating
Exceptional
(20 reviews)
Backyard Oasis, 3/1 Home w/ Hot Tub & Central AC
Santa Rosa, CA
8% off
Price is AU$5,893
AU$5,893
AU$842 per night
includes taxes & fees
Image gallery for Vineyard FarmStay w/ Heated Pool from May-Oct.
9.69.6 out of 10 rating
Exceptional
(23 reviews)
Vineyard FarmStay w/ Heated Pool from May-Oct.
Kenwood, CA
17% off
Price is AU$12,566
AU$12,566
AU$1,795 per night
includes taxes & fees
Image gallery for Wine Country Hideaway: 4BR, 2200Sf Rural Home With Solar-Heated Swimming Pool
1010 out of 10 rating
Exceptional
(81 reviews)
Wine Country Hideaway: 4BR, 2200Sf Rural Home With Solar-Heated Swimming Pool
Forestville, CA
8% off
Price is AU$9,878
AU$9,878
AU$1,411 per night
includes taxes & fees
Image gallery for Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills
Duncans Mills, CA
8% off
Price is AU$2,772
AU$2,772
AU$396 per night
includes taxes & fees
Image gallery for Sunny View Cottage in the Beautiful Wine Country
1010 out of 10 rating
Exceptional
(270 reviews)
Sunny View Cottage in the Beautiful Wine Country
Santa Rosa, CA
8% off
Price is AU$2,560
AU$2,560
AU$366 per night
includes taxes & fees
Image gallery for Spectacular & Secluded Wine Country Estate
1010 out of 10 rating
Exceptional
(14 reviews)
Spectacular & Secluded Wine Country Estate
Santa Rosa, CA
17% off
Price is AU$28,872
AU$28,872
AU$4,125 per night
includes taxes & fees
Image gallery for Spacious Modern Home - Pool, Views And Acres
9.49.4 out of 10 rating
Exceptional
(60 reviews)
Spacious Modern Home - Pool, Views And Acres
Cloverdale, CA
11% off
Price is AU$9,703
AU$9,703
AU$1,386 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$19,230
AU$19,230
AU$2,747 per night
includes taxes & fees
Image gallery for Welcome to the Soul Spa in Russian River Vacation Wonderland
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Welcome to the Soul Spa in Russian River Vacation Wonderland
Monte Rio, CA
8% off
Price is AU$4,782
AU$4,782
AU$683 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$6,876
AU$6,876
AU$982 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
(121 reviews)
Private Hilltop Vineyard Views! Luxury Home 6 Acres with private Pool & Hot Tub
Glen Ellen, CA
17% off
Price is AU$15,864
AU$15,864
AU$2,266 per night
includes taxes & fees
Image gallery for Wine Country Soulcation w/ Pool, Hot Tub & Game Room, Close to Wineries
1010 out of 10 rating
Exceptional
(7 reviews)
Wine Country Soulcation w/ Pool, Hot Tub & Game Room, Close to Wineries
Santa Rosa, CA
8% off
Price is AU$11,550
AU$11,550
AU$1,650 per night
includes taxes & fees
Image gallery for Lrg Wine Country Estate on creek w Pool/Spa sleeps 8
9.69.6 out of 10 rating
Exceptional
(34 reviews)
Lrg Wine Country Estate on creek w Pool/Spa sleeps 8
Glen Ellen, CA
16% off
Price is AU$7,086
AU$7,086
AU$1,012 per night
includes taxes & fees
Image gallery for Historic Van Keppel Ranch (Hot Tub, Scenic Views)
1010 out of 10 rating
Exceptional
(92 reviews)
Historic Van Keppel Ranch (Hot Tub, Scenic Views)
Santa Rosa, CA
16% off
Price is AU$13,053
AU$13,053
AU$1,865 per night
includes taxes & fees
Image gallery for Breathtaking Sonoma Country Vineyard Getaway
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Breathtaking Sonoma Country Vineyard Getaway
Occidental, CA
8% off
Price is AU$8,604
AU$8,604
AU$1,229 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
(16 reviews)
Fully Remodeled Private Wine Country Bungalow! Sunny Treetop Views, Luxury Beds
Forestville, CA
8% off
Price is AU$4,941
AU$4,941
AU$706 per night
includes taxes & fees
Image gallery for Sonoma Valley Wine Country Estate: Year-round Pool, Spa, Bocce, Fire Pit, Views
1010 out of 10 rating
Exceptional
(131 reviews)
Sonoma Valley Wine Country Estate: Year-round Pool, Spa, Bocce, Fire Pit, Views
Kenwood, CA
15% off
Price is AU$12,888
AU$12,888
AU$1,841 per night
includes taxes & fees
Image gallery for Relax in the most beautiful, secluded setting Sonoma County has to offer
1010 out of 10 rating
Exceptional
(46 reviews)
Relax in the most beautiful, secluded setting Sonoma County has to offer
Santa Rosa, CA
8% off
Price is AU$13,089
AU$13,089
AU$1,870 per night
includes taxes & fees
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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 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Wine Country Backyard Escape
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Modern Hilltop Healdsburg Residence With 360' Views
Sleeps 8 · 4 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
35 reviews(35 reviews)
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country
Sleeps 8 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
25 reviews(25 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