Chalk Hill Retreat
4 Bedrooms 3 Bathrooms House in Healdsburg
30 nt min

Property Details

We've always taken a proactive approach by thoroughly cleaning and disinfecting our homes prior to guest arrivals.  We’re now adding EMist electrostatic sprayers to apply EPA-approved disinfectants before and after our cleaners prepare houses for arrival Welcome home! Front entrance stairs to upper and lower levels Upper level landing from front entrance Upper landing looking toward dining area Kitchen with all cooking amenities. I'll Do The Dishes for THIS View! Gourmet Kitchen Appliances Gourmet Kitchen & Appliances Coffee Bar Accessories! Coffee bar window looking toward deck Kitchen Coffee Bar Dining area looking toward kitchen It's 5 o'clock somewhere! Living area looking into kitchen Living area and breakfast/game table Living area Bar Cart Master bedroom (king) Master Bath Master Bath Tub Master Bath Shower Bedroom 2 (Queen) Bedroom 3 (Queen) Bathroom 2 (shared) Bedroom 4 (lower level) Bathroom 3 (lower level) Family TV & game room on lower level Full Size Laundry Room (main level) Jacuzzi for relaxing! Expansive deck with lounge, fire pit and Weber BBQ grill Celebrate! Back Deck Looking Toward Jacuzzi 6 Burner Weber Grill Large back deck View From Jacuzzi Toward House Amazing views!

Property Description

This comfortable home in the woods along Chalk Hill Rd and in the Russian River AVA to the south of Healdsburg provides an excellent jumping off point for northern Sonoma & Napa County wine tasting adventures!

Property Details

***Property Available for Longer-Term Rental to Bay Area Families During COVID-19 Crisis***

Chalk Hill Retreat is situated on a wooded property on the western end of Chalk Hill and minutes from Highway 101 and the town of Windsor. The home is a lovely updated California craftsman style home on two levels. The main level is up a small flight from the front entrance while the lower level is down a flight. On the main level the house features a large open concept living room with a large kitchen and dining area. The kitchen is a gourmet style with all modern large and small appliances and a lounge eating area attached that open onto a large beautiful new deck.

The main level has three bedrooms and two bathrooms and a full laundry. The lower level features a private suite with bathroom and an activities room with air hockey table, mini Pac Man video machine and an assortment of games. The activities room opens onto its own private deck for lounging in the afternoon sun.

The home is smartly and whimsically decorated with colors, yet comfortable and welcoming. Guests receive a complementary bottle of wine and wine consultations.

The large entertaining deck overlooks a waterfall and sloped garden yard. One feels as though they are in a treehouse in a wooded oasis!


Mayastoga offers our guests Wine Country Concierge services for a small fee per day of your stay. Your concierge will plan and manage all aspects of your visit to our distinctive property in California’s northern Wine Country. Itineraries can include boutique and hard-to-access wineries, local restaurant reservations and transportation, as well as special touches that make for a truly memorable adventure. In addition to your tasting days, arrangements can include evenings in the comfort of your luxury residence with a private chef, a guest winemaker, or a cheese tasting and pairing with an internationally recognized food and wine expert (or all of the above!). Of course, there are numerous activities in addition to wine and culinary plans that are regularly arranged for our clients that include unique local attractions and activities (including our “Kids Country” itineraries).

TRAVEL INSURANCE: Please consider purchasing travel insurance for your upcoming reservation, especially if your reservation is from September to November. While travel insurance is not mandatory it does protect against an unforeseen trip cancellation due to:

- Named storms (tropical storms or hurricanes)
- Loss of job
- Sickness of family member
- Death of family member

Mayastoga Property Group has arranged with RentalGuardian to provide our guests with standard travel insurance at a costs of only 7% of your total invoice and CFAR (Cancel For Any Reason) travel insurance costs just 9.8%.

CANCELLATION POLICY: Effective March 1, 2020 our cancellation policy is as follows:
- Cancellations 30+ days prior to arrival will receive a full refund less any fees for credit card processing we assumed when you made your original payments. (We do not charge credit card fees when guests originally reserve)
- Cancellations less that 30 days prior to arrival will not receive a refund unless we are able to rebook the property for your same dates. In that case you will be refunded the full amount of your payments to date less any fees for credit card processing we assumed when you made your original payments. If we choose, you may be able to receive a credit toward a future stay valued at the full amount of your payments less original credit card fees.

Booking Calendar

Availability & Booking Calendar


Property Location




  • Concierge - Other Services
  • Housekeeper Optional
  • Massage - Other Services
  • Private Chef


  • Winery Tours


  • Games
  • Satellite / Cable
  • Stereo
  • Television


  • Air Conditioning
  • Central Heat
  • Clothes Dryer
  • Fireplace
  • Game Room
  • Garage
  • Hair Dryer
  • Internet - Wireless
  • Iron and Board
  • Linens Provided
  • Living Room
  • Parking
  • Telephone
  • Towels Provided
  • Washing Machine


  • Coffee Maker
  • Cookware
  • Dining Area
  • Dining Room
  • Dining Spices
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster


  • Bird Watching
  • Eco Tourism
  • Gambling
  • Horseback Riding
  • Outlet Shopping
  • Shopping
  • Wildlife Viewing


  • Fitness Center
  • Hospital
  • Laundromat


  • Mountain View
  • Near Ocean
  • Rural
  • Town


  • Balcony
  • Deck/Patio
  • Garden
  • Gas Grill


  • Hot Tub


  • Carbon Monoxide Detector
  • Deadbolt Lock
  • Emergency Exit Route
  • Fire Emergency Contact
  • Fire Extinguisher
  • First Aid Kit
  • Medical Emergency Contact
  • Outdoor Lighting
  • Police Emergency Contact
  • Smoke Detector


  • Family


30 nt min
- Rate varies due to seasonality and holidays.
- Please select your dates on our online booking calendar for an exact quote.


EV Charging Fee - $30.00 - Tax Exempt
Daily Housekeeping - Large Home - $175.00 - Tax Exempt
Small Child Cleaning Fee (6 YO and Under) - $225.00 - Tax Exempt
Mayastoga's Accidental Damage Insurance - $5,000 Coverage - $99.00 - Tax Exempt
Prep & Post-Stay Cleaning - $350.00 - Tax Exempt
Pet Accomodation & Cleaning - $350.00 - Tax Exempt
Damage Deposit - $2K - $2,000.00
Cancellation Policy
CANCELLATIONS (Large Homes) - A sixty (60) day notice is required for cancellation at 5+ bedroom homes. Cancellation sixty (60) days or more prior to the arrival date will incur no penalty. Cancellation less than sixty (60) days prior to arrival will result in forfeiture of fees paid. Reservation changes resulting in a shortened stay made less than sixty (60) days prior to arrival date will not be granted a reduced rental fee.

CANCELLATIONS (Small Homes) - A thirty (30) day notice is required for cancellation. Cancellation thirty (30) days or more prior to the arrival date will incur no penalty. Cancellation less than thirty (30) days prior to arrival will result in forfeiture of fees paid. Reservation changes resulting in a shortened stay made less than sixty (60) days prior to arrival date will not be granted a reduced rental fee.
This business is located in the United States of America.
Last updated 09/20/2020
Deposit Policy
DAMAGE WAIVER INSURANCE - Property damage insurance is required and will be added to your invoice total at time of booking. Renter acknowledges the he/she may be liable for damage above the coverage amount should any of the following cause significant harm to the property:

a. Damage is done to property or its contents, beyond normal wear and tear.
b. Debris other than toilet paper is placed in the toilets. The property is not connected to city sewer but has its own septic systems. Flushing feminine hygiene or other objects down the toilets can cause significant damage.
c. Debris, rubbish, recycle and discards are left in the house (must be placed in appropriate trash receptacles next to the small garage.)
d. Smoking in the house or anywhere on the property will result in a $1,000 fine NOT payable by the Damage Deposit Waiver.
e. Renter is evicted by the owner (or representative of the owner) or local law enforcement.
f. Having more than the approved number of people on the property at any one time without prior approval.
g. Adjusting any pool setting or equipment, water system (including sprinklers or well equipment, etc.), or any other property maintenance equipment.
Last updated 09/20/2020

Guest Reviews

Best Month in Paradise by Joshua & Marly D. 07/31/2020
We just departed the Chalk Hill Retreat after a month of sheer bliss. We wanted a nice get-away from the city during this crazy time and this home was a great option. Great access to both the Dry Creek and mountain wineries. Plenty of room, good internet and TV if you want it.
COVID Escape! by Laura C. 07/08/2020
We spent the month of June here and really enjoyed ourselves. The kitchen was obviously outfitted by a chef because they have EVERY gadget we ever wanted. We cook a lot! The BBQ is new and the fire pit on the deck is like being in a treehouse. We will definitely be back if school doesn't start this fall!
Tree House Deluxe by Shawna Y. 06/01/2020
This is like a brand new floors and freshly painted. We were a but skeptical because it lacked a pool, but we honestly never missed it. We LOVED the large deck and the feel of being up in the trees. The kids thought the Pac-man machine was the bomb. We all learned how to shoot the air hockey!
Neat Retreat by Peg K. 03/18/2020
What a great place...we spent an extended period at the retreat and just fell in love with the home and there area. Very close to Oliver's Market (Amazing grocery store in Windsor) and to some great wineries (The folks at Chalk Hill winery were very friendly and comped us our tasting because we’re neighbors), and coming home to the Retreat after exploring the area was so relaxing.
Spectacular Stay! by Bradley H. 11/25/2019
We stayed at Chalk Hill Retreat last month and truly enjoyed out visit. The house is well laid out and had all the amenities one would expect. We loved relaxing on the back deck after a Jacuzzi on many nights. The entire house was comfortable (including the beds!) and while we felt away from the crowds, we were close enough to both Healdsburg and Windsor to grab dinner then get home quickly. It's a lovely property and we will be back for our annual escape from the onset of the Eastern winter!