Holiday rentals near Chalk Hill Estate Vineyard
We found 1,512 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:7 Nov - 14 Nov
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 S$5,390
S$5,390
S$770 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 S$2,634
S$2,634
S$376 per night
includes taxes & fees
Image gallery for Sunny Poolside Winecountry Retreat
1010 out of 10 rating
Exceptional
(135 reviews)
Sunny Poolside Winecountry Retreat
Guerneville, CA
8% off
Price is S$4,684
S$4,684
S$669 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
18% off
Price is S$16,417
S$16,417
S$2,345 per night
includes taxes & fees
Image gallery for Pool Paradise in Wine Country!
1010 out of 10 rating
Exceptional
(13 reviews)
Pool Paradise in Wine Country!
Kenwood, CA
8% off
Price is S$8,347
S$8,347
S$1,192 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 S$4,019
S$4,019
S$574 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
12% off
Price is S$17,066
S$17,066
S$2,438 per night
includes taxes & fees
Image gallery for Norcal Hideaway
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Norcal Hideaway
Guerneville, CA
8% off
Price is S$3,670
S$3,670
S$524 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 S$4,005
S$4,005
S$572 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 S$9,175
S$9,175
S$1,311 per night
includes taxes & fees
Image gallery for Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8
1010 out of 10 rating
Exceptional
(22 reviews)
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8
Santa Rosa, CA
8% off
Price is S$11,709
S$11,709
S$1,673 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$2,196
S$2,196
S$314 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 S$2,054
S$2,054
S$293 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$8,179
S$8,179
S$1,168 per night
includes taxes & fees
Image gallery for Backyard Oasis, 3/1 Home w/ Hot Tub & Central AC
1010 out of 10 rating
Exceptional
(21 reviews)
Backyard Oasis, 3/1 Home w/ Hot Tub & Central AC
Santa Rosa, CA
8% off
Price is S$4,467
S$4,467
S$638 per night
includes taxes & fees
Image gallery for Spectacular & Secluded Wine Country Estate
1010 out of 10 rating
Exceptional
(16 reviews)
Spectacular & Secluded Wine Country Estate
Santa Rosa, CA
16% off
Price is S$26,232
S$26,232
S$3,747 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 S$4,812
S$4,812
S$687 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 S$2,128
S$2,128
S$304 per night
includes taxes & fees
Image gallery for Starview Lodge: Quiet Mountain Home Bordering State Forest
9.49.4 out of 10 rating
Exceptional
(131 reviews)
Starview Lodge: Quiet Mountain Home Bordering State Forest
Cobb, CA
7% off
Price is S$2,286
S$2,286
S$327 per night
includes taxes & fees
Image gallery for Grapevine Cottage by AvantStay | Hobby Vineyard, Firepit, Ample Outdoor Seating
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Grapevine Cottage by AvantStay | Hobby Vineyard, Firepit, Ample Outdoor Seating
Glen Ellen, CA
6% off
Price is S$3,793
S$3,793
S$542 per night
includes taxes & fees
Image gallery for Spacious Modern Home - Pool, Views And Acres
9.49.4 out of 10 rating
Exceptional
(62 reviews)
Spacious Modern Home - Pool, Views And Acres
Cloverdale, CA
11% off
Price is S$8,438
S$8,438
S$1,205 per night
includes taxes & fees
Image gallery for 'Moonview Ranch' on 20 Acres in Sonoma County!
9.69.6 out of 10 rating
Exceptional
(33 reviews)
'Moonview Ranch' on 20 Acres in Sonoma County!
Sebastopol, CA
7% off
Price is S$2,029
S$2,029
S$290 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 S$2,334
S$2,334
S$333 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 S$10,136
S$10,136
S$1,448 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
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 | Complimentary wine 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