4 bedrooms
•
4 beds
•
3.5 bathrooms
•
8 guests
•
New
•
3993.4069 sq. ft.
Operated by a Wander partner
Trusted operators, vetted by Wander
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.
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1 king bed
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1 king bed
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1 king bed
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1 king bed
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1 king bed
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Cloverdale, California 95425, United States
Cloverdale, California, United StatesFree cancellation up to 14 days before check-in. No refund after that.
Pets not allowed
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
8 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Nov 12, 2026 | $1164 | Not Available |
| Nov 13, 2026 | $1294 | Available |
| Nov 14, 2026 | $1295 | Available |
| Nov 15, 2026 | $1159 | Available |
| Nov 16, 2026 | $961 | Available |
| Nov 17, 2026 | $960 | Available |
| Nov 18, 2026 | $1165 | Available |
| Nov 19, 2026 | $1240 | Not Available |
| Nov 20, 2026 | $1348 | Not Available |
| Nov 21, 2026 | $1840 | Not Available |
| Nov 22, 2026 | $1840 | Not Available |
| Nov 23, 2026 | $1265 | Available |
| Nov 24, 2026 | $1840 | Not Available |
| Nov 25, 2026 | $2121 | Not Available |
| Nov 26, 2026 | $2200 | Not Available |
| Nov 27, 2026 | $1924 | Not Available |
| Nov 28, 2026 | $1840 | Not Available |
| Nov 29, 2026 | $1510 | Available |
| Nov 30, 2026 | $1306 | Available |
| Dec 1, 2026 | $1038 | Available |
| Dec 2, 2026 | $1263 | Available |
| Dec 3, 2026 | $1313 | Available |
| Dec 4, 2026 | $1426 | Available |
| Dec 5, 2026 | $1380 | Available |
| Dec 6, 2026 | $1236 | Available |
| Dec 7, 2026 | $1104 | Available |
| Dec 8, 2026 | $1006 | Available |
| Dec 9, 2026 | $1018 | Available |
| Dec 10, 2026 | $1102 | Not Available |
| Dec 11, 2026 | $1303 | Not Available |
| Dec 12, 2026 | $1299 | Not Available |
| Dec 13, 2026 | $1249 | Available |
| Dec 14, 2026 | $1253 | Available |
| Dec 15, 2026 | $1144 | Available |
| Dec 16, 2026 | $1233 | Available |
| Dec 17, 2026 | $1402 | Available |
| Dec 18, 2026 | $1532 | Available |
| Dec 19, 2026 | $1492 | Available |
| Dec 20, 2026 | $1467 | Available |
| Dec 21, 2026 | $1468 | Available |
| Dec 22, 2026 | $1665 | Not Available |
| Dec 23, 2026 | $1582 | Not Available |
| Dec 24, 2026 | $2092 | Not Available |
| Dec 25, 2026 | $2064 | Not Available |
| Dec 26, 2026 | $1725 | Available |
| Dec 27, 2026 | $1759 | Available |
| Dec 28, 2026 | $1895 | Available |
| Dec 29, 2026 | $2275 | Available |
| Dec 30, 2026 | $2434 | Available |
| Dec 31, 2026 | $2806 | Available |
| Jan 1, 2027 | $2675 | Available |
| Jan 2, 2027 | $1801 | Available |
| Jan 3, 2027 | $2207 | Available |
| Jan 4, 2027 | $1681 | Available |
| Jan 5, 2027 | $1318 | Available |
| Jan 6, 2027 | $1134 | Available |
| Jan 7, 2027 | $1255 | Available |
| Jan 8, 2027 | $1513 | Available |
| Jan 9, 2027 | $1505 | Available |
| Jan 10, 2027 | $1270 | Available |
| Jan 11, 2027 | $1182 | Available |
| Jan 12, 2027 | $1080 | Available |
| Jan 13, 2027 | $1456 | Available |
| Jan 14, 2027 | $1415 | Available |
| Jan 15, 2027 | $1997 | Not Available |
| Jan 16, 2027 | $1892 | Not Available |
| Jan 17, 2027 | $1667 | Not Available |
| Jan 18, 2027 | $1125 | Available |
| Jan 19, 2027 | $863 | Available |
| Jan 20, 2027 | $963 | Available |
| Jan 21, 2027 | $1265 | Available |
| Jan 22, 2027 | $1537 | Available |
| Jan 23, 2027 | $1555 | Available |
| Jan 24, 2027 | $1423 | Available |
| Jan 25, 2027 | $1244 | Available |
| Jan 26, 2027 | $1002 | Available |
| Jan 27, 2027 | $1002 | Available |
| Jan 28, 2027 | $1277 | Available |
| Jan 29, 2027 | $1642 | Available |
| Jan 30, 2027 | $1771 | Available |
| Jan 31, 2027 | $1475 | Available |
| Feb 1, 2027 | $1118 | Available |
| Feb 2, 2027 | $1261 | Available |
| Feb 3, 2027 | $1254 | Available |
| Feb 4, 2027 | $1453 | Available |
| Feb 5, 2027 | $1573 | Available |
| Feb 6, 2027 | $1528 | Available |
| Feb 7, 2027 | $1424 | Available |
| Feb 8, 2027 | $1369 | Available |
| Feb 9, 2027 | $1387 | Available |
| Feb 10, 2027 | $1322 | Available |