Photo by Jennifer Hill

Chalk Hill Vacation Rentals

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Vacation Rentals 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

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

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (414)
"This is the second time we have brought friends to the property. It is very clean and homey. We love sitting and watching the ocean, the fireplace was wonderful since it was cold outside. Walked on the beach and ate a few meals out. Looking forward to going back again, it is the perfect getaway!!"
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (358)
"A cozy magical little spot where you feel like all the beauty around is just for you. All the amenities made for a relaxing stay. We miss it already!"
Oceanfront - Hot Tub - Newly Remodeled Cottage

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

10.0 out of 10, Exceptional, (59)
"Villa Montebella is a wonderful place for a large group. Our families stayed at the Villa over the Thanksgiving Holiday week to celebrate our Daughter’s Napa Wedding. The pictures are accurate, but do not do the property justice. The place is Stunning! There are many comfortable and secluded bedrooms and facilities. The wine cave was amazing and we hired Chef Adair for a special rehearsal dinner there. We have an active group and took advantage of the many amenities. The media room was perfect...
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

9.8 out of 10, Exceptional, (305)
"We had a lovely relaxing stay at Jujube, and hope to be back again soon. Thank you Bridgette!"
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

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

Luxury Napa Estate With Pool/Hot-tub/Concierge

10.0 out of 10, Exceptional, (40)
"This property is simply amazing from the special touches and decorations that welcomed us for my daughter‘s bachelorette weekend to the recommendations of chef Misty Phelps all the touches were just simply above and beyond. We thoroughly enjoyed ourselves and had a wonderful time."
The price is CA $1,520
CA $2,674 total
includes taxes & fees
Feb 25 - Feb 26
Luxury Napa Estate With Pool/Hot-tub/Concierge

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

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!!!

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

Valley of the Moon Getaway

10.0 out of 10, Exceptional, (222)
"Most beautiful place I have ever stayed. Everything you could want or need. "
Valley of the Moon Getaway

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!

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, (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 CA $713
CA $1,293 total
includes taxes & fees
Jan 31 - Feb 1
Ocean view easy access to Doran Beach, Golf course and Bluewater Bistro.

Iconia: Historic Mansion, Heated Pool & Hot Tub, 9 Bedrooms

10.0 out of 10, Exceptional, (4)
"One of a kind property in a beautiful location. The layout was super well suited for our group, with lots of spaces to relax and enjoy each other's time. The host is great - very responsive and kind, with all the amenities you need/expect. Would love to stay at this property again. Thank you so much!"
Iconia: Historic Mansion, Heated Pool & Hot Tub, 9 Bedrooms

4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

9.2 out of 10, Wonderful, (163)
"This property was as advertised. Met or exceeded our expectations. Nice neighborhood."
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

King Non-vaulted Ceiling

8.0 out of 10, Very good, (2)
"Expedia communication was horrible. Did not list address or lodging name. Room was great once we called for details."
The price is CA $212
CA $280 total
includes taxes & fees
Feb 5 - Feb 6
King Non-vaulted Ceiling
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 types of properties in Chalk Hill you may be interested in

Holiday Inn Windsor Wine Country, an IHG Hotel

3.0 star property
9.0 out of 10, Wonderful, (851)
"NA"
The price is CA $154
CA $176 total
includes taxes & fees
Feb 9 - Feb 10
Holiday Inn Windsor Wine Country, an IHG Hotel

Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

2.5 star property
9.0 out of 10, Wonderful, (1006)
"Yeah, great, lower price than most and quality breakfast, good WiFi, secure parking lot. Only issue is room access there’s only one door, one elevator, so if on the end of halls, it’s a lot of walking back and forth. Otherwise though, great"
The price is CA $145
CA $166 total
includes taxes & fees
Feb 28 - Mar 1
Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 star property
9.2 out of 10, Wonderful, (1002)
"First time staying there it was so calm and peaceful."
The price is CA $189
CA $215 total
includes taxes & fees
Feb 28 - Mar 1
Hampton Inn & Suites Windsor - Sonoma Wine Country
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.