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Compare 52 Villas in Chalk Hill with updated reviews, rates, and availability.

Valley of the Moon Getaway
Outdoor dining
Valley of the Moon Getaway
10.0 out of 10, Exceptional, (210)
"This property was absolutely beautiful. We actually altered dinner reservations so we could enjoy the outdoors and the views. Highly recommmed. Linda and he husband were incredibly gracious hosts. "
Valley of the Moon Getaway
Wellington by AvantStay | Secluded Wine Country Estate w/ Gorgeous Mtn Views
Welcome to Wellington.
Wellington by AvantStay | Secluded Wine Country Estate w/ Gorgeous Mtn Views
9.6 out of 10, Exceptional, (15)
"We had a wonderful time at this home. I would recommend it to most everyone. Great location, check in was smooth, beautiful spacious home with lots to do even on rainy days. The fireplaces provide coziness and comfort. Beds were great! I will provide my constructive criticism, the home needed a bit of attention to detail. When you looked out into the backyard. The hose was old and flung across the property. There were random broken planters and orange cones. It was distracting from the beauty of...
Wellington by AvantStay | Secluded Wine Country Estate w/ Gorgeous Mtn Views
Villa Vista, The Absolute Jewel of Jenner
A stunning water view of river and ocean greets you as soon as you enter.
Villa Vista, The Absolute Jewel of Jenner
10.0 out of 10, Exceptional, (41)
"This was the most charming rental with fabulous views of the Russian River and the Pacific. It is best for a couple because the one bath is in the primary bedroom. The design, especially the kitchen is drop-dead gorgeous. I would love to return."
Villa Vista, The Absolute Jewel of Jenner
Gorgeous Napa estate 15 mins to St Helena surrounded by vineyards. Permit 138485
Property exterior
Gorgeous Napa estate 15 mins to St Helena surrounded by vineyards. Permit 138485
10.0 out of 10, Exceptional, (6)
"What a delightful place for a family get together! Very well equipped home in a vineyard on Howell Mountain. Host could not have been more accommodating. We enjoyed exploring the grounds and vineyard as well as the pool and outdoor deck and grill. Looking forward to our next visit on Howell Mountain!! Thank you Ricardo for sharing your home with us."
Gorgeous Napa estate 15 mins to St Helena surrounded by vineyards. Permit 138485
Iconia: Historic Mansion, Heated Pool & Hot Tub, 9 Bedrooms
Iconia: Historic Mansion, Heated Pool & Hot Tub, 9 Bedrooms
10.0 out of 10, Exceptional, (3)
"The house was everything we wanted it to be. The hosts were communicative and very helpful. They suggested nearby restaurants and golf courses for our guests. We will definitely entertain at this house again. "
Iconia: Historic Mansion, Heated Pool & Hot Tub, 9 Bedrooms
Year-Round Heated Pool | Hot Tub | Fire Pit | Lawn
The spacious grounds feature comfortable seating around the pool and on the oversized deck overlooking vineyards.
Year-Round Heated Pool | Hot Tub | Fire Pit | Lawn
10.0 out of 10, Exceptional, (27)
"Our party of six loved this property! We even opted for one less wine tour so we'd have more time to hangout poolside. The layout, inside and out, is optimal for a group. We even had fresh pears for breakfast (off the trees out back). 10-minute walk to a fun bar/restaurant. Only a short drive to wineries. James is a great host! We will be back!!"
Year-Round Heated Pool | Hot Tub | Fire Pit | Lawn
Luxury Napa Estate With Pool/Hot-tub/Concierge
Luxury Napa Estate With Pool/Hot-tub/Concierge
10.0 out of 10, Exceptional, (35)
"We LOVE staying at this location. Such a hidden absolute GEM! Saloni, Nicole, Esperanza, all such lovely people to work and communicate with. We can't wait for our next stay!!"
Luxury Napa Estate With Pool/Hot-tub/Concierge
Stunning Villa in the Heart of Sonoma County
Stunning Villa in the Heart of Sonoma County
9.8 out of 10, Exceptional, (83)
" Wonderful stay at the Villa, the views are breathtaking and the home was a great place to relax and cook a meal after a long day of wine tasting. "
Stunning Villa in the Heart of Sonoma County
Belleza by AvantStay | Hilltop Mansion w/ Pool & Ultra Modern Interior
Infinity pool with gorgeous views.
Belleza by AvantStay | Hilltop Mansion w/ Pool & Ultra Modern Interior
10.0 out of 10, Exceptional, (2)
"My friends and I loved this beautiful home! The outdoor areas were great. We barbecued in the outdoor kitchen and made pizzas twice in the out door pizza oven. The few issues we had during our visit were addressed very quickly by the owner and management team. We are all already talking about coming back next year!"
Belleza by AvantStay | Hilltop Mansion w/ Pool & Ultra Modern Interior
Stunning Country Retreat, Pool, Hottub, Views, 92 Acres
Pool House Pool, relax in the shady arbor
Stunning Country Retreat, Pool, Hottub, Views, 92 Acres
9.6 out of 10, Exceptional, (14)
"Nice space for a big group. We spent most of our time in the farm house because that is where the majority of the group slept. Pool house is very nice and spacious."
Stunning Country Retreat, Pool, Hottub, Views, 92 Acres
Heart of Sonoma County, Fountain Grove 4BR/4BA home, pool, spa, outdoor kitchen
Pool
Heart of Sonoma County, Fountain Grove 4BR/4BA home, pool, spa, outdoor kitchen
10.0 out of 10, Exceptional, (1)
"This was a perfect space to come back to after a full day of wine tasting and exploring the Valley. Very spacious, clean, and accommodating of all our needs. The host was prompt with any questions we had and the entire process was as seamless as could be. We will certainly be coming back! Just an amazing property."
Heart of Sonoma County, Fountain Grove 4BR/4BA home, pool, spa, outdoor kitchen
Exceptional Estate Vineyards in Healdsburg Sonoma County
Dining
Exceptional Estate Vineyards in Healdsburg Sonoma County
8.0 out of 10, Very Good, (1)
"Beautiful property, excellent host and easy check-in, check-out and communications. Wasn't clear until we arrived that the spa was off limits. Could have been a bit cleaner and provided a little better bath amenities. However, well-stocked kitchen and wonderful outdoor living spaces-we were able to put together a great meal to enjoy all of the wine we bought throughout the day. We would stay again and hope to enjoy a full wine tasting at the property on our next trip out."
Exceptional Estate Vineyards in Healdsburg Sonoma County
Entire Wine Country Resort Villa #Pool-Spa-Tennis-Wine-Dine#
Terrace/patio
Entire Wine Country Resort Villa #Pool-Spa-Tennis-Wine-Dine#
10.0 out of 10, Exceptional, (17)
"This was the perfect house for my friends and I to have an extended weekend to celebrate my birthday. The location is remote and quiet, but close to everything. We did wine tastings two of the days, and it didn't take very long to get anywhere we went. The house is beautiful. We used the pool a bit on the afternoon of the very hot day. We didn't use the sport court, it was too hot, but it's there. The house was well stocked. We used the guest house as well, it was perfect. "
Entire Wine Country Resort Villa #Pool-Spa-Tennis-Wine-Dine#
Mountain Serenity: Luxe Pool, Views, Comfort
Mountain Serenity: Luxe Pool, Views, Comfort
10.0 out of 10, Exceptional, (2)
"We had an amazing time here and pictures are exactly as it is in real life. Hosts were very kind and responsive. Would love to comeback!"
Mountain Serenity: Luxe Pool, Views, Comfort
Estrella by AvantStay | Secluded Spanish-Style Estate on 7 Acres of Vineyards
A large outdoor pool.
Estrella by AvantStay | Secluded Spanish-Style Estate on 7 Acres of Vineyards
8.6 out of 10, Excellent, (14)
"This was a family reunion with family from the Bay Area and from the UK. We have stayed at this property before, and we were pleased with the upgrades to the kitchen area. Our stay was magical. The privacy in the extensive grounds, the beautiful pool and well-appointed house set the scene for a great visit. Minor problems with the pool and hot water were attended to immediately by the property management team. We are recommending Estrella to friends who are looking for a similar arrangement"
Estrella by AvantStay | Secluded Spanish-Style Estate on 7 Acres of Vineyards
Pool, 3 Acres, Pool Table, Hot Tub
Soak in the hot tub!
Pool, 3 Acres, Pool Table, Hot Tub
9.8 out of 10, Exceptional, (30)
"This was our destination the property so beautiful we never left and we didn't have to this place had it all and if it didn't we had great restaurants and groceries delivered right to us. The pool was the main attraction plus ample space to spread out and relax and enjoy. Awe spent evenings in the garden, playing pool and rejuvenating in the jacuzzi. We will be coming back."
Pool, 3 Acres, Pool Table, Hot Tub
You Will Dream of this House AND its Views!
You Will Dream of this House AND its Views!
9.4 out of 10, Exceptional, (8)
"Everything about this house was truly spectacular. The views were breathtaking, the house was very modern but inviting with every detail thought of. Comfortable family room perfect for our family of 5 adults to watch movies and play games. The kitchen was fully stocked which made it easy to grill/cook meals. We enjoyed the house and pool so much we decided to eat more meals at home than out. We definitely enjoyed every moment of our stay and hope to return some day!! "
You Will Dream of this House AND its Views!
Titan: Theater, Heated Pool, Gym, Billiards
Large outdoor area directly accessible from the family room (pool table room) and gym.
Titan: Theater, Heated Pool, Gym, Billiards
9.2 out of 10, Wonderful, (5)
"Three generations of our family gathered here for 4 fabulous days. We relaxed and played in the pool/hot tub, watched movies in the theatre, took advantage of the nearby restaurants and spent a fun afternoon at Safari West. The house has a wonderful, airy layout with lots of cool spaces to hang out together or alone. Host went above and beyond to make sure we enjoyed an stress-free time. Highly recommend!!"
Titan: Theater, Heated Pool, Gym, Billiards
Locanda Winery estate with Olympic-size pool & Starlink WiFi - dog-friendly
Locanda Winery estate with Olympic-size pool & Starlink WiFi - dog-friendly
9.6 out of 10, Exceptional, (26)
"This Property is absolutely Gorgeous! We loved the home and location. I would check in with the management company if I were the owner. Master shower clogged and won’t drain which has caused wall damage. Our two guest rooms had dirty towels and ours were wet. Home is fabulous!!"
Locanda Winery estate with Olympic-size pool & Starlink WiFi - dog-friendly
Sky View: All-Season Heated Pool & Hot Tub, 5 Acres, EV Plug
Sky View: All-Season Heated Pool & Hot Tub, 5 Acres, EV Plug
10.0 out of 10, Exceptional, (22)
"Our family had a blessed time! We lived in the pool and played a ton of pool. Lots of sweet family memories."
The price is SAR 2,031
SAR 4,099 total
includes taxes & fees
8 Oct - 9 Oct
Sky View: All-Season Heated Pool & Hot Tub, 5 Acres, EV Plug
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chalk Hill

Cottage home near the Russian River; county parks; numerous wineries
Dining
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (89)
"Great house, no issues. "
Cottage home near the Russian River; county parks; numerous wineries
Chalk Hill Cottage Close to Wineries
Chalk Hill Cottage Close to Wineries
9.8 out of 10, Exceptional, (24)
"The cottage is very nice and well appointed, with all the needed amenities and more! Very convenient location to visit local wineries and the town of Healdsburg. It was very easy to communicate with our hosts as well. We had a great stay!"
Chalk Hill Cottage Close to Wineries
Stunning Home with Pool, Hot Tub, Decks, & Gourmet Kitchen - Close to Wineries
Stunning Home with Pool, Hot Tub, Decks, & Gourmet Kitchen - Close to Wineries
9.2 out of 10, Wonderful, (88)
"Cleanliness could have been better ( lots of cobwebs and dead flies in the tub) but we enjoyed the property."
Stunning Home with Pool, Hot Tub, Decks, & Gourmet Kitchen - Close to Wineries
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.