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Compare 835 Vacation Homes in Chalk Hill with updated reviews, rates, and availability.

Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

10.0 out of 10, Exceptional, (233)
"We have stayed in properties in many cities. This is one of the finest we have ever experienced. We could not ask for a better vacation home. MMichael "
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

Wine Country Getaway

10.0 out of 10, Exceptional, (18)
"This was our second time staying at this home with my family of 6. You just can’t beat it. It is beautiful designed and cared for. The beds are so comfortable and my kids love the “robot” toilets. It is private and a great location. Will be back again soon "
The price is AED 878
AED 2,144 total
includes taxes & fees
29 Jan - 30 Jan
Wine Country Getaway

5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

9.8 out of 10, Exceptional, (22)
"We loved our 2-night stay. We especially loved that each person in our group had their own bedroom (and bathroom). The house is beautifully designed with comfortable beds and couches. The living/dining room has gorgeous massive ceilings. We also loved the huge dining table for meals/games, etc. The aesthetic throughout the house was right up the alley of our group. Everything you need is provided and has been thoughtfully curated. Every room was well-appointed and very clean.The hot tub...
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

The Best value on the River and Great Low Season 20% Discounts Available

9.4 out of 10, Exceptional, (88)
"Great location, comfortable house, there were a few maintenance issues and we got locked out of the house (code stopped working on the door) before our check out time. Luckily there were people still in the house to let us back in."
The Best value on the River and Great Low Season 20% Discounts Available

Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country

10.0 out of 10, Exceptional, (120)
"Loved the property, right on the water, very clean, well stocked for cooking in. Highly recommend.My only complaint is the laundry list of check out items… we were only there for a short weekend and had to launder all towels before leaving with incredibly specific instructions about cycle length and amount of detergent, etc. our checkout was at 11am… it was a little stressful to get it all done. if we’re paying a few hundred for a cleaning service, shouldn’t that include laundering towels? Or...
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country

Wine Country Backyard Escape

10.0 out of 10, Exceptional, (14)
"We had a wonderful stay! The backyard was perfect for eating outside, relaxing in the hot tub and playing bocce. Our little dogs loved the freedom to run and play in the fenced yard."
Wine Country Backyard Escape

Kenwood Vista by AvantStay | 7acres w/ Pool, Fire Pit, Vineyard Views

10.0 out of 10, Exceptional, (1)
"Simply amazing, the pictures and descriptions of the house, property, and area tell the story but if anything, understate the experience.We were already planning to revisit in the Spring within the first day of being there. The house was perfect for our family and everything was just right from the smooth check-in all the way down to the sheets and pillows. But it was the outdoors that sets it above the rest with the pool/hot tub, fire-pit, and outdoor table area being just right and the view...
Kenwood Vista by AvantStay | 7acres w/ Pool, Fire Pit, Vineyard Views

COZY Bungalow--Dog-Friendly—Perfect for Couples!!!

9.6 out of 10, Exceptional, (159)
"Everything went great. The location is very convenient for hiking and restaurants. Everything is a short drivee away. Pamela was very helpful and allowed us to come in earlier than the check in time. She had wonderful suggestions for restaurants and hikes in the area. The bed was very comfortable and the location was very quiet. The kitchen had all that we needed including a nice supply of spices. We had excellent meals at the following:Fisheterian - Lunch - We had the fish tacos and...
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!

Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

10.0 out of 10, Exceptional, (127)
"Don’t hesitate to book this place! Amazing 360 views, gorgeous house that’s even bigger and nicer than the photos. The owner Per is super nice and communicative. Everything in the house is top of the line. We loved it!"
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

10.0 out of 10, Exceptional, (218)
"Our family getaway to Lavender Hill was definitely one to remember.  This was for a joint birthday celebration for sister and mom, the perfect coming together place for our three families, ages ranging from 3yo to 80yo.  We enjoyed our time making meals together in the spacious kitchen and countless hours spent outdoors - on the swings, court, around the fire pit, in the hot tub, and exploring the overall grounds.  William was a fantastic host, so incredibly kind and thoughtful.  Extremely...
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

1 Acre with 3 homes in the heart of wine country with last minute specials!

9.6 out of 10, Exceptional, (28)
"A group of 11 stayed at this property over a long weekend and enjoyed our stay. The location was great, everything we needed was very easy to get to. It was nice that we could all stay together while still having our space when we needed. "
1 Acre with 3 homes in the heart of wine country with last minute specials!

Ocean view easy access to Doran Beach, Golf course and Bluewater Bistro.

10.0 out of 10, Exceptional, (69)
"This home is filled with high-end amenities and ocean or golf course views from every window. The property manager was easy to reach and we plan to stay here when we visit the area again. "
The price is AED 1,653
AED 3,088 total
includes taxes & fees
28 Jan - 29 Jan
Ocean view easy access to Doran Beach, Golf course and Bluewater Bistro.

Tranquil home with free WiFi and full kitchen

9.6 out of 10, Exceptional, (45)
"Views were beautiful. Loved the kitchen and honestly I have 0 faults with my stay….. wished it was longer"
Tranquil home with free WiFi and full kitchen

Bird Watch @ Land's End with Amazing Views of the Harbor and Pacific Ocean

10.0 out of 10, Exceptional, (122)
"Very beautiful place everything about it was special "
Bird Watch @ Land's End with Amazing Views of the Harbor and Pacific Ocean

Home near golf course, close to Healdsburg

10.0 out of 10, Exceptional, (28)
"Great house and location"
Home near golf course, close to Healdsburg

Casa Rosa Summary:<br>Th

10.0 out of 10, Exceptional, (28)
"This house is wonderful and very comfortable for 4 couples.Location is perfect and can walk to most of the restaurants. We will rent again ! Patty"
Casa Rosa Summary:<br>Th

Calistoga Vineyard House

10.0 out of 10, Exceptional, (33)
"This was a killer place and will be back. "
Calistoga Vineyard House

Annadel House Retreat- Stunning Wine Country Luxe!

9.4 out of 10, Exceptional, (27)
"We had a fantastic time with five ladies from across the country to celebrate two 50th birthdays. The place was fantastic – the kitchen was great for cooking a meal and for coffee in the morning. Plenty of space to spread out & the beds were comfortable!!!! We had a minor issue with the showerheads being scaled with water. We reached out to the property owner and while they didn’t fix it on our visit 6 pounds of salt were dropped off so I assume they are fixing it for the next guest. Highly...
The price is AED 1,245
AED 2,986 total
includes taxes & fees
3 Feb - 4 Feb
Annadel House Retreat- Stunning Wine Country Luxe!

Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

9.4 out of 10, Exceptional, (323)
"This was our second time in Bodega Bay. This location was great. My husband was able to fish and go and I was able to relax. The owner is nice. It was clean and had every thing you need. Also close to restaurants and stores. I do not want to stay no where else when we return. We were right on the water. "
The price is AED 937
AED 2,041 total
includes taxes & fees
28 Jan - 29 Jan
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

New Modern House in Sonoma Valley's Best Area

10.0 out of 10, Exceptional, (240)
"We were highly pleased with this vacation rental. It is much better than what shown in the pictures. Very relaxing comfortable tastefully decorated cottage with gorgeous views. Host is professionally caring and responsive. Thank you for sharing your place and allowing us to have a memorable time there. "
New Modern House in Sonoma Valley's Best Area
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

5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

9.8 out of 10, Exceptional, (22)
"We loved our 2-night stay. We especially loved that each person in our group had their own bedroom (and bathroom). The house is beautifully designed with comfortable beds and couches. The living/dining room has gorgeous massive ceilings. We also loved the huge dining table for meals/games, etc. The aesthetic throughout the house was right up the alley of our group. Everything you need is provided and has been thoughtfully curated. Every room was well-appointed and very clean.The hot tub...
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

Cottage home near the Russian River; county parks; numerous wineries

10.0 out of 10, Exceptional, (92)
"Property was perfect for me while I was taking care of my grandchildren"
Cottage home near the Russian River; county parks; numerous wineries

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (31)
"We spent 3 nights at Beaux Maison Sonoma Cottage and my wife and I loved it. Very comfy, well equipped and loved the fire pit it the evenings. And the location was great too - on Chalk Hill Road, so in the country but only 15 minutes from Healdsburg and close to many wineries. And only 35 minutes to Calistoga. For future trips for just the two of us, would definitely try to stay again!"
Chalk Hill Cottage 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.