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Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg

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A residential property with a curved driveway, stone walls, and palm trees.
A large house with a circular driveway, surrounded by trees and a view of a distant town.
A dining area with a large table, chairs, and a view through the glass doors.
Interior
A hotel room with a large bed, a desk, and a chair. There is a window with a view of greenery outside.

Popular amenities

  • Pool
  • Hot tub
  • Air conditioning
  • Parking available
  • Fireplace

Explore the area

View in a map
Healdsburg, CA
  • Place, Simi Winery
    ‪16 min walk‬
  • Place, Krug Event Center
    ‪2 min drive‬
  • Place, Healdsburg Ridge Open Space Preserve
    ‪5 min drive‬
  • Airport, Santa Rosa, CA (STS-Sonoma County)
    ‪19 min drive‬

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  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
9.6 out of 10, Exceptional, 70 reviews
$462 nightly
The price is $527
Nov 15 - Nov 16
Total with taxes and fees
The Madrona

About the neighborhood

Healdsburg

Located within a mile (2 km) of Simi Winery, this villa is within 2 miles (3 km) of Krug Event Center. The villa includes a private pool, a fireplace, and a TV.
View more Villas in HealdsburgOpens in a new window

What's nearby

  • Simi Winery - 16 min walk - 0.8 miles
  • Krug Event Center - 2 min drive - 1.1 miles
  • Healdsburg Plaza - 3 min drive - 2.0 miles
  • Healdsburg Ridge Open Space Preserve - 5 min drive - 1.4 miles
  • Dry Creek Vineyard - 8 min drive - 5.5 miles

Getting around

  • Santa Rosa Station - 20 min drive
  • Santa Rosa, CA (STS-Sonoma County) - 20 min drive

Restaurants

  • ‪Hazel Hill - ‬7 min drive
  • ‪Villa Chanticleer - ‬8 min drive
  • ‪Costeaux French Bakery - ‬6 min drive
  • ‪Folia Bar & Kitchen - ‬5 min drive
  • ‪Ridge Vineyards - Lytton Springs - ‬6 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg

Wake up to sweeping Wine Country views in this peaceful hilltop boutique hotel room, designed for couples seeking privacy and comfort. The Overlook Room features a private entrance, queen bed with luxury linens, fast Wi-Fi, climate control, and free on-site parking.
Just minutes from downtown Healdsburg, you’ll enjoy easy access to world-class wineries, tasting rooms, restaurants, and shops, then return to a quiet, serene setting above town. Perfect after a day of wine tasting, hiking, or dining out.

Guests love the easy self check-in, calm surroundings, and the feeling of a romantic Wine Country escape without sacrificing convenience.
Ideal for: romantic getaways, wine tasting weekends, couples trips, and relaxing Sonoma County stays.
The villa is air-conditioned and has an array of amenities, including a private pool, a fireplace, and an ironing board. The villa also includes a hair dryer.

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Exterior
Healdsburg Luxury Villa Estate | Private Boutique Stay Near Plaza & Wineries
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  • Pool
  • Hot tub
  • Kitchen
  • Pet friendly
$2,008 nightly
The price is $2,267
Nov 12 - Nov 13
Total with taxes and fees
Healdsburg Luxury Villa Estate | Private Boutique Stay Near Plaza & Wineries

Property amenities

Pool/Spa

  • Hot tub
  • Private pool

Internet

  • Available in the villa: Internet access

Parking and transportation

  • Parking on site

Bedrooms

  • 1 bedroom
  • Bed sheets provided

Bathroom

  • Hair dryer

Living spaces

  • Fireplace

Entertainment

  • TV

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Property does not allow children

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

An adult age 18 or older must assume all liability for the booking
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Remove personal items
Turn off the lights, lock the doors, and return the keys
Failure to complete these may result in a negative review from the host.

Pets

  • This property doesn't allow pets

Children and extra beds

  • This property doesn't allow children

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.

Property is also known as

31157

Frequently asked questions

What is there to do close to this villa?

This villa is located in Healdsburg, close to Healdsburg Plaza, Mazzocco Winery, and SingleThread Farm at Dry Creek. You'll also find Russian River and Healdsburg Center for the Arts within a short drive.

How much does it cost to stay at Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg?

As of Nov 11, 2026, prices found for a 1-night stay for 2 adults at Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg on Nov 16, 2026 start from $416, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is there parking available at Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg?

No, this villa doesn't offer parking.

Is this villa adjacent to a casino?

No, this villa is not connected to a casino.

Is there an indoor pool at this villa?

No, this villa doesn't have an indoor pool; however, there is a hot tub.

What amenities will couples enjoy at Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg?

There are many amenities for couples at this villa, including a private pool and a fireplace in each villa with some featuring a private pool.

Does Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg have a hot tub?

No, this villa doesn't have a spa tub.

Does this villa offer breakfast?

No, this villa doesn't offer breakfast.

Does this villa allow pets to stay for free?

No, pets aren't allowed at this villa.

Does Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg have connecting rooms available?

No, this villa doesn't feature connecting guestrooms.

How far is the airport from this villa?

The closest major airport to this villa is Santa Rosa, CA (STS-Sonoma County), which is 12.9 mi away (20 minutes by car).

Are there rooms with balconies at Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg?

No, you won't find villas with balconies at Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg.

Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg Reviews