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Home in Cloverdale, California

Oak & Sky Ranch

4 bedrooms

4 beds

3.5 bathrooms

8 guests

New

3993.4069 sq. ft.

Operated by a Wander partner

Trusted operators, vetted by Wander

About the property

Fall brings golden hillsides and crisp starlit nights to Alexander Valley, and this 44 acre hilltop estate is built for savoring both with family or friends. Four king suites, a chef's kitchen, a stargazing hot tub, and a private pool and pickleball court keep everyone close and comfortable, just 25 minutes from Healdsburg Plaza. Request your dates and start planning your Wine Country gathering.

Oak & Sky Ranch is a refreshed and reimagined wine country farmhouse with more than 4,000 square feet of living space on 44 private acres. The house is invisible from the street, reached by a half mile private road from the gate.

The Kitchen
The heart of the house. Cathedral ceilings with exposed wood beams and skylights frame a huge marble island with a gas cooktop built for communal cooking, a second sink, a second dishwasher and a wine refrigerator. Around the perimeter you'll find a 64 inch double refrigerator, two built in ovens, a farmhouse sink and a dishwasher. The butler's pantry adds a third sink, a second refrigerator, extra counter space and the washer and dryer.

Living and Dining
The kitchen opens to a large dining room under a chandelier, with a sliding door to a covered, screened deck for alfresco dinners or morning coffee. Two separate living and entertainment areas let different groups watch their own movies, sports or kids' shows. The sunroom has panoramic views over the Alexander Valley and is perfect for yoga.

Bedrooms (4 king beds, 3.5 baths)
Primary suite: main level, modern king bed, very large walk in shower, quick access to the wrap around porch and sunroom.
Upstairs bedrooms (2): each with a king bed and epic views over the Alexander Valley and the oak studded hills, sharing a large bathroom between them with a modern soaking tub, a large shower and two sinks.
Loft suite: a separate, very private suite above the garage with a king bed and its own bathroom.
Every bedroom has a workstation for remote work. The first floor has central heating and air, and each upstairs bedroom has its own mini split.

Outdoors
Eco pool (unheated) with a large surrounding deck, misters, umbrellas and a pool cover. Hot tub placed for stargazing. Propane fire pit circled by Adirondack chairs, with a BBQ grill alongside. Screened wrap around porch with egg chairs, shuffleboard and ceiling fans. Private Flexcourt pickleball court and basketball hoop.

The Barns
The Play Barn is a converted barn and stable with a 74 inch smart TV and soundbar, pool table, foosball, darts, wine barrel bar tables, a second BBQ grill and a covered bocce court. The Art Barn has gallery walls, exposed beams and flexible lounge seating for yoga, private tastings or workshops.

Tech
Starlink internet with a mesh network throughout the house and Play Barn, an AT&T cell signal booster, and five smart TVs.

Parking
A large driveway with plenty of open parking plus two carports that each cover two cars. RV parking with water, electric and sewer hookups is available on request. A Level 2 EV charger outside the garage is available for guest use.

Wine Country without the driving: book our 11 passenger wine tour van or 6 passenger Cadillac Escalade for tastings, dinners or airport pickups.

Oak & Sky Ranch sleeps 8 overnight guests in 4 king beds. Children under 3 do not count toward the guest total. Up to 14 guests are welcome during the daytime, and events are welcome within Sonoma County regulations with prior written approval. Up to four pets are welcome, with a pet fee of $400 per pet. Pets may never be left unattended in the home, including while crated. Please disclose all pets when booking. Smoking is not permitted anywhere on the property.

This is a rural estate at the wildlife interface. Deer visit often, and there are reports of mountain lions, coyotes and, in spring, snakes. Never leave small children out of sight or pets unsupervised. Two gentle older horses, owned by a neighbor, graze the pastures; you are welcome to pet them but please do not feed or ride them. The seasonal pond is not for swimming, and the steep ravine to the west is off limits.

Internet is via Starlink satellite, which is fast but may have brief outages.

Check in is 4:00 PM and check out is 10:00 AM. Quiet hours are 9:00 PM to 7:00 AM. The minimum booking age is 25. Exterior cameras, used mainly for wildfire monitoring, are located at the gate, on the driveway facing north, on the roof facing west, and at the upper barn facing east.

Early check ins and late check outs are subject to availability, must be approved in writing in advance, and are charged at 50% of the nightly rate.

Property licenses: TVR22-0093, LIC24-0204, PMR26-0051. County tax number 4393N.

Property License: LIC24-0204

Where you’ll sleep

Bedroom

1 king bed

Bedroom

1 king bed

Bedroom

1 king bed

Bedroom

1 king bed

Bedroom

1 king bed

Bedroom

1 king bed

Bedroom

1 king bed

Bedroom

1 king bed

Amenities

Common Amenities

  • Outdoor pool
  • Hot tub
  • BBQ Area
  • Air conditioning
  • Bathtub
  • Bed linens
  • Cooking basics
  • Dishes
  • Dishwasher
  • Dryer
  • Toys
  • Free parking
  • Garden
  • Heating
  • Wifi
  • Kitchen
  • Dedicated workspace
  • Oven
  • Pool table
  • Fridge
  • Smoke detector
  • Stove
  • TV
  • Washer

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Where you’ll be

Cloverdale, California 95425, United States

Cloverdale, California, United States
38.8326731-123.0031225
Timezone: America/Los_Angeles

Things to know

Cancellation policy

Free cancellation up to 14 days before check-in. No refund after that.

Property rules

Pets not allowed

No smoking - fees will apply

Events not allowed

Safety & security

Check-in after 4:00 pm

Check-out before 10:00 am

8 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Nov 12, 2026$1164Not Available
Nov 13, 2026$1294Available
Nov 14, 2026$1295Available
Nov 15, 2026$1159Available
Nov 16, 2026$961Available
Nov 17, 2026$960Available
Nov 18, 2026$1165Available
Nov 19, 2026$1240Not Available
Nov 20, 2026$1348Not Available
Nov 21, 2026$1840Not Available
Nov 22, 2026$1840Not Available
Nov 23, 2026$1265Available
Nov 24, 2026$1840Not Available
Nov 25, 2026$2121Not Available
Nov 26, 2026$2200Not Available
Nov 27, 2026$1924Not Available
Nov 28, 2026$1840Not Available
Nov 29, 2026$1510Available
Nov 30, 2026$1306Available
Dec 1, 2026$1038Available
Dec 2, 2026$1263Available
Dec 3, 2026$1313Available
Dec 4, 2026$1426Available
Dec 5, 2026$1380Available
Dec 6, 2026$1236Available
Dec 7, 2026$1104Available
Dec 8, 2026$1006Available
Dec 9, 2026$1018Available
Dec 10, 2026$1102Not Available
Dec 11, 2026$1303Not Available
Dec 12, 2026$1299Not Available
Dec 13, 2026$1249Available
Dec 14, 2026$1253Available
Dec 15, 2026$1144Available
Dec 16, 2026$1233Available
Dec 17, 2026$1402Available
Dec 18, 2026$1532Available
Dec 19, 2026$1492Available
Dec 20, 2026$1467Available
Dec 21, 2026$1468Available
Dec 22, 2026$1665Not Available
Dec 23, 2026$1582Not Available
Dec 24, 2026$2092Not Available
Dec 25, 2026$2064Not Available
Dec 26, 2026$1725Available
Dec 27, 2026$1759Available
Dec 28, 2026$1895Available
Dec 29, 2026$2275Available
Dec 30, 2026$2434Available
Dec 31, 2026$2806Available
Jan 1, 2027$2675Available
Jan 2, 2027$1801Available
Jan 3, 2027$2207Available
Jan 4, 2027$1681Available
Jan 5, 2027$1318Available
Jan 6, 2027$1134Available
Jan 7, 2027$1255Available
Jan 8, 2027$1513Available
Jan 9, 2027$1505Available
Jan 10, 2027$1270Available
Jan 11, 2027$1182Available
Jan 12, 2027$1080Available
Jan 13, 2027$1456Available
Jan 14, 2027$1415Available
Jan 15, 2027$1997Not Available
Jan 16, 2027$1892Not Available
Jan 17, 2027$1667Not Available
Jan 18, 2027$1125Available
Jan 19, 2027$863Available
Jan 20, 2027$963Available
Jan 21, 2027$1265Available
Jan 22, 2027$1537Available
Jan 23, 2027$1555Available
Jan 24, 2027$1423Available
Jan 25, 2027$1244Available
Jan 26, 2027$1002Available
Jan 27, 2027$1002Available
Jan 28, 2027$1277Available
Jan 29, 2027$1642Available
Jan 30, 2027$1771Available
Jan 31, 2027$1475Available
Feb 1, 2027$1118Available
Feb 2, 2027$1261Available
Feb 3, 2027$1254Available
Feb 4, 2027$1453Available
Feb 5, 2027$1573Available
Feb 6, 2027$1528Available
Feb 7, 2027$1424Available
Feb 8, 2027$1369Available
Feb 9, 2027$1387Available
Feb 10, 2027$1322Available