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Compare 845 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, (236)
"Great friends, great house, great memories!We could not have asked for more."
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

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

Wine Country Getaway

10.0 out of 10, Exceptional, (19)
"This is a very nice open floor plan home with many upgraded amenities. The location is perfect for exploring western Sonoma and there is a nice, but modest grocery store just two blocks away. The only minor issue is that the driveway is short and quite steep which may challenge some drivers."
The price is SAR 896
SAR 2,174 total
includes taxes & fees
1 Mar - 2 Mar
Wine Country Getaway

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, (15)
"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, (2)
"Incredible location, views and appointments in house. We cooked there and the kitchen was great. The views are amazing and the pictures almost don’t do it justice. We would absolutely rent this place again. It was an incredible place."
Kenwood Vista by AvantStay | 7acres w/ Pool, Fire Pit, Vineyard Views

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

9.6 out of 10, Exceptional, (162)
"Excellent location to be near bodega bay restaurants and The headlands -very nice and approachable host, very dog friendly place. "
COZY Bungalow--Dog-Friendly—Perfect for Couples!!!

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

10.0 out of 10, Exceptional, (219)
"Lavender Hill was the perfect spot for a weekend reunion with a bunch of friends to celebrate a milestone birthday! The home is beautiful and has everything you need for a great stay. The panoramic views were breathtaking and our group spent the majority of our stay in the living area soaking up the beauty. We had grand plans for making more use of the sport court and would've loved to use the pool (it was too cold), but this just makes it easier to plan a return stay in the future. Thanks to...
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, (29)
"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!

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

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

10.0 out of 10, Exceptional, (70)
"The house was very warm and comfortable. Clean and had just about everything we needed. Close walk to the beach and relaxing views"
Ocean view easy access to Doran Beach, Golf course and Bluewater Bistro.

Calistoga Vineyard House

10.0 out of 10, Exceptional, (34)
"Nice new place with great kitchen."
Calistoga Vineyard House

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

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

Home near golf course, close to Healdsburg

10.0 out of 10, Exceptional, (28)
"Wow. We loved everything about this place. As comfortable as home. Fantastic location for lots of wineries. Windsor is a cute town. Nothing is very far. Best part was have a waffle maker to make our traditional Christmas morning waffles. Will definitely stay again. "
Home near golf course, close to Healdsburg

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 SAR 1,271
SAR 3,016 total
includes taxes & fees
24 Feb - 25 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, (324)
"Great views, lots to see and close to vineyards "
The price is SAR 956
SAR 2,084 total
includes taxes & fees
25 Feb - 26 Feb
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

Waterfront 3bed and 2bath home with panoramic ocean views

10.0 out of 10, Exceptional, (2)
"Really enjoyed our selves, great location, great view and a very nice Deli/store down the block. We will be back! "
Waterfront 3bed and 2bath home with panoramic ocean views

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
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

Gable by AvantStay | Beautiful 3.5 Acre Oasis w/ Gorgeous Views, Pool & Hot Tub

9.2 out of 10, Wonderful, (10)
"We had a good time. Kitchen well equipped but could be brighter in dining area as mentioned in other reviews. WI-FI was off most of the time which did cause some problems for our group. Spa was nice "
Gable by AvantStay | Beautiful 3.5 Acre Oasis w/ Gorgeous Views, Pool & Hot Tub

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
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.