
Vacation rentals near Chalk Hill Estate Vineyard
We found 1,512 vacation rentals — enter your dates for availability
Choose the right private vacation rental within close proximity to Chalk Hill Estate Vineyard. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as WiFi and a pool. At the end of the day, you'll find a rental for everyone's needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - Chalk Hill Estate Vineyard
Showing deals for:Nov 7 - Nov 14
Image gallery for TandaTula, Wine Country Sanctuary with Pool, Hot Tub, Bocce, Fire Pits and More!

1010 out of 10 rating
Exceptional
(126 reviews)
TandaTula, Wine Country Sanctuary with Pool, Hot Tub, Bocce, Fire Pits and More!
Healdsburg, CA
5% off
Price is CA $2,104
CA $2,104
CA $18,056 total
CA $18,056 total
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
15% off
Price is CA $292
CA $292
CA $2,815 total
CA $2,815 total
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
10% off
Price is CA $610
CA $610
CA $5,832 total
CA $5,832 total
includes taxes & fees
Image gallery for Rivers Breeze | Complimentary wine tasting at Croix included!

1010 out of 10 rating
Exceptional
(14 reviews)
Rivers Breeze | Complimentary wine tasting at Croix included!
Healdsburg, CA
5% off
Price is CA $473
CA $473
CA $4,707 total
CA $4,707 total
includes taxes & fees
Image gallery for Sunny Poolside Winecountry Retreat

1010 out of 10 rating
Exceptional
(135 reviews)
Sunny Poolside Winecountry Retreat
Guerneville, CA
10% off
Price is CA $526
CA $526
CA $5,063 total
CA $5,063 total
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
20% off
Price is CA $2,139
CA $2,139
CA $16,299 total
CA $16,299 total
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
10% off
Price is CA $962
CA $962
CA $8,672 total
CA $8,672 total
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
33% off
Price is CA $514
CA $514
CA $4,332 total
CA $4,332 total
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
15% off
Price is CA $1,999
CA $1,999
CA $17,087 total
CA $17,087 total
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
10% off
Price is CA $477
CA $477
CA $4,310 total
CA $4,310 total
includes taxes & fees
Image gallery for Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

1010 out of 10 rating
Exceptional
(64 reviews)
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella
Glen Ellen, CA
5% off
Price is CA $3,324
CA $3,324
CA $31,850 total
CA $31,850 total
includes taxes & fees
Image gallery for Norcal Hideaway

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Norcal Hideaway
Guerneville, CA
10% off
Price is CA $423
CA $423
CA $3,936 total
CA $3,936 total
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
10% off
Price is CA $1,053
CA $1,053
CA $9,431 total
CA $9,431 total
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
19% off
Price is CA $250
CA $250
CA $2,348 total
CA $2,348 total
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
10% off
Price is CA $254
CA $254
CA $2,195 total
CA $2,195 total
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
19% off
Price is CA $991
CA $991
CA $8,418 total
CA $8,418 total
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
10% off
Price is CA $1,350
CA $1,350
CA $11,809 total
CA $11,809 total
includes taxes & fees
Image gallery for ✨River View Lodge | Complimentary wine tasting at Croix included!

9.69.6 out of 10 rating
Exceptional
(70 reviews)
✨River View Lodge | Complimentary wine tasting at Croix included!
Healdsburg, CA
5% off
Price is CA $744
CA $744
CA $7,116 total
CA $7,116 total
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
10% off
Price is CA $525
CA $525
CA $4,827 total
CA $4,827 total
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
10% off
Price is CA $557
CA $557
CA $5,202 total
CA $5,202 total
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
10% off
Price is CA $248
CA $248
CA $2,273 total
CA $2,273 total
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
20% off
Price is CA $3,082
CA $3,082
CA $26,009 total
CA $26,009 total
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
10% off
Price is CA $1,138
CA $1,138
CA $10,423 total
CA $10,423 total
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
10% off
Price is CA $253
CA $253
CA $2,445 total
CA $2,445 total
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 · 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)
Top rated rentals - Chalk Hill Estate Vineyard
This must be heaven …
1010 out of 10
Exceptionalexceptional
169 reviews(169 reviews)
The house was even more beautiful than the photos show! My friends and I were breathless when we arrived from the amazing views, the gorgeous furnishings and the personal touches, including lovely art, music playing throughout the home and fresh flowers in several rooms. Everything was of the finest quality including the linens, mattresses and even the dishes and cookware. The location of the home was perfect for offering a tranquil retreat after enjoying everything the area has to offer. Sally was super helpful and a pleasure to deal with. My party and I hope to return to her amazing property!
Andrea T.
Stayed May 2024
Enjoyed our family stay
1010 out of 10
Exceptionalexceptional
242 reviews(242 reviews)
Lovely property and convenient.
Bruce O.
Stayed May 2024
Casa Mona
1010 out of 10
Exceptionalexceptional
149 reviews(149 reviews)
Beautiful central location, comfortable and clean. Just slightly dated.
div g.
Stayed Mar 2024
Wonderful Stay
1010 out of 10
Exceptionalexceptional
92 reviews(92 reviews)
This is the nicest VRBO I have ever stayed in with the kindest and most considerate hosts. The property is well kept and extraordinary, offering privacy and proximity to Sebastopol. It was an easy walk into the town. Everything was very well maintained and the location is quiet and private. I cannot wait to return, and I cannot thank the hosts enough for their care, attention to detail and thoughtfulness.
S. J.
Stayed Oct 2023
Great!
1010 out of 10
Exceptionalexceptional
96 reviews(96 reviews)
Great house! The view, the SPA and all activities around are great
Martin L.
Stayed Aug 2023
Heaven on Earth
1010 out of 10
Exceptionalexceptional
58 reviews(58 reviews)
Just a beautiful week in St Helena. A short walk to town. The accommodation was very well equipped, we were wanting for nothing. Beautiful front porch as well as a lovely backyard.
Thank you so much 😊
Brian B.
Stayed May 2023
Northern Napa Brilliance
1010 out of 10
Exceptionalexceptional
178 reviews(178 reviews)
Great spot, quiet, sunsets over the mountain and vineyard. This is 100x better than a hotel stay and only a few minutes down a beautiful winding road from Calistoga or St. Helena
Would highly recommend.
Ryan S.
Stayed Sep 2022
Gorgeous view - well located - well equipped property
1010 out of 10
Exceptionalexceptional
82 reviews(82 reviews)
Easy communication with owner - good service - well located and well equipped
Dominique M.
Stayed Nov 2021
- 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, yards and more
- More for lessMore space, more privacy, more amenities — more value