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  • Exterior
  • Pool & Outdoor Dining
  • Pool & Patio
  • Pool & Patio
  • Great Room
  • Great Room
  • Great Room
  • Great Room
  • Great Room
  • Family Room
  • Family Room
  • Family Room
  • Kitchen
  • Kitchen
  • Great Room
  • Dining Room
  • Dining Room
  • Wet Bar
  • Breakfast Nook
  • Patio
  • Pool
  • Patio
  • Primary Bedroom
  • Primary Bedroom
  • Primary Bathroom
  • Bedroom 2
  • Bedroom 3
  • Bedroom 3
  • Bedroom 4
  • Bedroom 4
  • Guest House Living Area
  • Bedroom 5
  • Pool & Patio
  • Exterior
  • Patio
4.8 · 49 reviews
Inspirato Residence

Winner's Circle

Sonoma County, California
10
5
5.5
8,270 sqft

Set on an idyllic hilltop with 360-degree views, this expansive five-bedroom home pairs chic mid-century modern design with floor-to-ceiling windows and abundant natural light. Multiple patios, a heated lap pool, in-pool hot tub, and detached guest house make the most of its Wine Country setting.

Book with confidence

Five king bedrooms with en suite baths provide privacy for groups, while a gourmet kitchen, formal dining room, and fireside library offer generous spaces to gather. Russian River Valley wineries are just minutes away, with downtown Healdsburg approximately 20–30 minutes by car.

  • Countryside views
  • Guest cottage
  • Private pool
  • Vineyards nearby

  • Full-service stay — on-site concierge & housekeeping

  • Pre-trip planning — custom itinerary built before you go

  • Ready on arrival — groceries stocked before you land

Features & Amenities

  • Minutes from the Russian River Valley’s wineries, and 20-30 minutes from downtown Healdsburg
  • Heated outdoor lap pool and in-pool hot tub
  • Multiple patios with dining furniture, lounge chairs, and umbrellas
  • Chic, mid-century modern design by renowned local interior designer
  • Gourmet kitchen featuring KitchenAid and Sub-Zero appliances
  • Formal dining room and additional breakfast nook
  • Large library with seating and wood-burning fireplace
  • Skylights and floor-to-ceiling windows
  • En suite bathrooms for all bedrooms
  • Grill
  • Air conditioning
  • Sonos sound system

Amenities

  • Air Conditioning
  • Hot Tub
  • Pool

Bedding

  • Primary Bedroom

    • One King Bed

  • Bedroom 2

    • One King Bed

  • Bedroom 3

    • One King Bed

  • Bedroom 4

    • One King Bed

  • Bedroom 5

    • One King Bed

Floor plans

Explore 3D Tour

Know before you go

check-in time
check-out time

  • This home is exclusively staffed, managed, and maintained by Inspirato.
  • Bedroom 5 is the detached, 830-square-foot guest house includes a bedroom, living room with queen-sized sleeper sofa, and kitchenette, and is located adjacent to the main house—just a short walk down a covered sidewalk connecting the two buildings.
  • This home has five full bathrooms and one half-bathroom.
  • Sonoma County code restricts the total maximum number of guests and visitors at this home at any one time from 7 a.m.-10 p.m. Please contact your Destination Planner for details.
  • The surrounding vineyards are separate properties and privately owned by wineries. Members do not have access to walk, run or explore the vineyards.

Additional Information:

  • Cancellation policy: The Standard Inspirato Cancellation Policy applies for this property. The Peak Reservation policy applies for Christmas and New Year’s weeks and certain other travel dates.
  • Maximum occupancy: Stated occupancy cannot be exceeded.
  • Pet policy: No pets allowed.

Members-Only Benefits:

  • Skip the baggage hassle by using Ship&Play, which offers door-to-door transport for your luggage and sports equipment.
  • Enjoy unique Inspirato tasting experiences at Inspirato’s partner wineries in the area.
Have questions?
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(888) 625-7525

Location

We recommend arriving via Santa Rosa Sonoma County Airport (STS), just a 15-minute drive from Winner’s Circle. You can also fly into San Francisco International Airport (SFO) or Oakland International Airport (OAK). The drive from either of these airports is about 90 minutes to two hours.

Winner’s Circle is located in the countryside, so we recommend a rental car through Club partner Avis, as taxis and ride-sharing services are not reliable. If you are visiting wineries and tastings, your Destination Concierge is happy to arrange a driver or bicycle rentals.

Need help booking flights? Our luxury airfare concierge can book your preferred seats and flight times at the best available price.

Reviews

1 - 5 of 49 reviews

Tina S

Large home but very tired

The home is large and great open spaces for gathering. However it is very tired and worn. It needs a refresh. Bathrooms aren't adequate and the home overall feels like it isn't well constructed. The finishes just aren't great. Also the location is really far from most places people want to visit in Napa and Sonoma wine tasting. There are places in Sonoma that are easier to reach but if you want to visit Napa this isn't the right location for you.

Anonymous

Not a winner

The house was in a nice location with beautiful views and all the beds were comfortable but the home was very outdated. The bathrooms had water damage, very old fixtures and appliances and the jacuzzi would not heat over 93*. The heater would keep shutting off. A couple of the sliding doors would not lock as well. I would not stay there again, definitely would go to a different property. -CM

John H

Winners Circle Vacation

We have used this house a number of times for friends and family vacations. It is beautiful and ideal for celebrations or family gatherings, It provides great access to all of the wonders of the area including redwoods, the Bedoga Coast, wineries from all the areas, cheese makers, and excellent restaurants/caterers. The conceriege is teriffic, Chefs Eric and Laura Lee provide excellent meals and classes on food and wine, and Cork Dork provides Limo services, Full Package

James W

Great House, Great Location

The house is spectacularly located and perfect for a large party. It is 15-20 minutes from a lot of wineries, towns, hikes. Located on a hill in the middle of a vineyard. Hot tub and pool and lots of natural light. Was a wonderful house. Staff is amazing. Loved every minute of it.

Anonymous

Beautiful Wine Country Experience

The Winner's Circle is an absolutely beautiful property. We were a group of 5 women and there was ample room for each of us to have our own bedroom and bathroom, which were lovely and well appointed. The views from the property are stunning and the house had all of the amenities we needed - we had a chef cook onsite for dinner, a wine tasting experience delivered in the house (Croix Winery), and in-home massages as well. Brittany did an outstanding job of pulling our ever-evolving itinerary together and Judith was a responsive and reliable on-site concierge. We really enjoyed the pool and hot tub and took full advantage of all of the features of the house (fantastic Sonos sound system, great library, wonderful space). I would definitely book this house again.