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Healdsburg Vacation Rentals

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Vacation Rentals (21)

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Dry Creek Moderna
Dry Creek Moderna
    Price: €801/night €4,806/week €18,689/month
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 3
    • Contact Manager

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Jimtown House
Jimtown House
Contact Manager
Nightly rate from
€244
4.5 of 5 stars 6 reviews
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 2
This restored country home sits in the Alexander Valley near the famous Jimtown store, and looks across to and around vineyards. Just 7 minutes from Central ...
  • Nightly
    €244
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Redwood Tree House Riverfront Home
Redwood Tree House Riverfront Home
Contact Owner
4 of 5 stars 1 review
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 2
Nestled in a picturesque redwood grove on the banks of the Russian River, only 3 miles from historic Healdsburg Plaza, Redwood Tree House is one of the most ...
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Redwood Cottage
Redwood Cottage
Contact Manager
Nightly rate from
€97
4.5 of 5 stars 6 reviews
Management: Professional
Property: Rental Home
Bedrooms: 1, sleeps 2
Bathrooms: 1
Redwood Cottage is a studio cabin nestled in a beautifully forested area, located in the hills of Dry Creek Valley, approximately 6.5 miles from central ...
  • Nightly
    €97
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Stillerus
Stillerus
Contact Manager
Nightly rate from
€278
4 of 5 stars 8 reviews
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 10
Bathrooms: 2
Need to get away from it all? City life driving you crazy? Escape to blissful tranquility in this charming getaway venue in Sonoma County's Dry Creek Valley. ...
  • Nightly
    €278
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Villa Ariadna
Villa Ariadna
Contact Manager
Nightly rate from
€416
4 of 5 stars 1 review
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 4
Welcome to Villa Ariadna. This attractive ranch estate is set on acres of vineyard, hillside, and beautiful green lawn and fruit trees. Located on a country ...
  • Nightly
    €416
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Interlude
Interlude
Contact Manager
Nightly rate from
€384
4 of 5 stars 1 review
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 7
Bathrooms: 2
Interlude is a pleasant wine country cottage just 10 minutes from Central Healdsburg, 5 minutes to Old Town Windsor, or 20 minutes to Guerneville/Russian ...
  • Nightly
    €384 - €433
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Picnic Cottage
Picnic Cottage
Contact Manager
Nightly rate from
€141
4 of 5 stars 1 review
Management: Professional
Property: Rental Home
Bedrooms: 1, sleeps 2
Bathrooms: 1
Ten minutes from the busy downtown Healdsburg area, Picnic Cottage is located on a hillside with views to the Dry Creek Valley. Crushed granite walkways, deck ...
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    €141
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Retreat at Dry Creek Valley
Retreat at Dry Creek Valley
Contact Manager
Nightly rate from
€197
4 of 5 stars 2 reviews
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 4
Bathrooms: 2
Incredible top of the world views to Dry Creek Valley, Healdsburg and Santa Rosa Valleys from this mountain top retreat. Fifteen minutes from the 101 freeway ...
  • Nightly
    €197
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Mill Creek Cottage
Mill Creek Cottage
Contact Manager
Nightly rate from
€106
4 of 5 stars 2 reviews
Management: Professional
Property: Rental Home
Bedrooms: 1, sleeps 4
Bathrooms: 1
Mill Creek Cottage is less than 10 minutes to the Healdsburg Plaza Square. Located in a gated and park like setting, this cottage is extra roomy for 2-4 ...
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    €106 - €141
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Twin Oak
Twin Oak
Contact Manager
Nightly rate from
€416
3.5 of 5 stars 1 review
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 10
Bathrooms: 4
Twin Oak is a beautiful 62 acre property which combines the charm of a turn of the century home with all the comforts of modern ammenities. We start with the ...
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    €416 - €519
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Heaven in the Redwoods
Heaven in the Redwoods
Contact Manager
Nightly rate from
€244
3.5 of 5 stars 2 reviews
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 11
Bathrooms: 3
A truely serene setting that is a wonderful and special retreat in Sonoma County Wine Country. From the moment you drive through the gate and onto 'Heaven in ...
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    €244
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Valley Oak Manor
Valley Oak Manor
Contact Manager
Nightly rate from
€312
3.5 of 5 stars 7 reviews
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 10
Bathrooms: 2
Valley Oak Manor is a lovely country home located in the Heart of the Dry Creek Valley wine growing area in Healdsburg. Set slightly elevated on a knoll, this ...
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    €312
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RIVER RANCH RENTALS (SLPS 16) 2 homes 100ft apart
RIVER RANCH RENTALS (SLPS 16) 2 homes 100ft apart
Contact Owner
Management: Verified owner
Property: Rental Home
Bedrooms: 6, sleeps 16
Bathrooms: 6
Less than a mile from the town plaza of Healdsburg, w/600ft on the beautiful Russian River. 90+ vineyards and wineries with in 5 miles of our ranch. OAK TREE ...
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Lincoln Street Bungalow in Healdsburg
Lincoln Street Bungalow in Healdsburg
Contact Manager
Nightly rate from
€200
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 6
Bathrooms: 2
Lincoln Street Bungalow is a beautifully remodeled California Bungalow with beautiful hardwood floors, custom lighting, gourmet island kitchen, front porch ...
  • Nightly
    €200
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La Casa de Agua Tranquillo
La Casa de Agua Tranquillo
Contact Manager
Nightly rate from
€1,335
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 10
Bathrooms: 5
It's all about the setting here. Let's begin with the Spanish style villa design of the main house with 3300 square feet, a bell tower that actually rings in ...
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    €1,335
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Felta Lodge in Healdsburg
Felta Lodge in Healdsburg
Contact Manager
Nightly rate from
€622
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 11
Bathrooms: 5
Felta Lodge is an extraordinary property set in beautifully landscaped grounds, featuring vineyard views, in ground pool, hot tub, gazebo, multiple decks for ...
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    €622 - €828
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Vintage Hills
Vintage Hills
Contact Manager
Nightly rate from
€312
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 3
This Vintage Hills location is less than 10 minutes to the plaza square in Healdsburg, and near wineries such as Simi, and the famous Dry Creek Valley and ...
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    €312 - €416
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Wine Country Cottage
Wine Country Cottage
Contact Manager
Nightly rate from
€192
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 6
Bathrooms: 1
This lovely little cottage is really a unique and hard to find category for a few guests or 2 couples. Furnished smartly, and priced right, this cottage ...
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    €192 - €244
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Lake Sonoma Estate
Lake Sonoma Estate
Contact Manager
Nightly rate from
€1,001
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 12
Bathrooms: 6
Lake Sonoma Estate is a property that may come along once every 2-3 years as an offering for vacation rental accommodations. This home sits on a hilltop with ...
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    €1,001 - €1,335
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Healdsburg Vacation Rental Advice
50th Birthday/how to spend it in sonoma area?
Posted by Alongforthetrip, Aug 14, 2009
... Would you have a specific rental or two in Sea Ranch to recommend? I've learned the hard way that "what you see is not necessarily what you get" when looking at a place online and have had a vacation or two diminished because of that. Let me know what ... more
Posted by Alongforthetrip, Aug 17, 2009
... and advice! I'm leaning toward the Wine Country Weekend. I would love to stay at Honor, but it's financially out of my reach! I've been looking at rental homes in the area. I need to/will make up my mind tonight on when and where to stay ... more
itinerary help
Posted by SWIRLSIFFSIP, Jun 18, 2009
... highly recommend staying at a vacation home rental...or even ... ... possible! contact the sonoma county vacations team and ... ... take care! all of their vacation homes are on here and as you can see from the reviews, its a trustworthy company. www.sonomacountyvacations.com or 800-454-6674 and 707-433 ... more
Posted by getmeoutoftherain, Jun 18, 2009
... like it will be a vacation rental. I ... ... amazing wines. We enjoy taking our time for breakfast then enjoy appetizers and a glass of wine at night so having a vacation rental lends itself to that. So now..suggestions for vacation rental (I'm already onto VRBO) and wineries. Thanks ... more
Del Rio Woods Beach
Posted by riovino, Jan 25, 2007
... are almost always nice and quiet. Regarding passage of canoes & kayaks, I believe there was a lawsuit in the 1970's between the local canoe rental company and some homeowners, but this hasn't been an issue for many many years....canoes, kayaks and whatever flow by all day. Matt ... more
Posted by riovino, Jan 25, 2007
Glad I could help. If they don't have availability let me know. I also have a vacation rental at Del Rio Woods Beach, although it's not directly on the water. Good luck and let me know if you need additional info about the area. ... more
Posted by Middle_Aged_Man, Jan 26, 2007
... stab here riovino, and guess that your rental property is the one listed as "Rio Vino"? (Pretty darn Sherlock Holmesian of me to figure that one out, eh?) If the riverside cottage I am looking at doesn't work out, I'll be sure to call on you! Again, thanks ... more
Healdsburg Modern cottages
Posted by HPROPMGMT, Oct 20, 2007
... being out). The tradeoff on vacation rental is more privacy, and not having to be on anyone's schedule, regarding breakfast, cleaning, etc., however for those guests that want the true hotel experience, I can understand where there might be some let down. I just wanted to make sure reviewers ... more
Posted by Chris_and_Erin, May 6, 2008
... Having a kitchen was also a nice plus, we were able to heat up some of our delicious leftovers from the restaurants and sit by the fire place with a glass of wine, something you usually can't do when on vacation. You can't go wrong with these cottages ... more
Lodging help in northern wine country!
Posted by marykect, Jan 28, 2008
... looking for some sort of rental lodging in ... ... with kitchen amenities. Nothing fancy, just two comfortable bedrooms and a kitchen to make breakfast and sandwiches for the day. Any dinner recommendations welcome. We plan to be in the area for 4-6 days in mid-May with a rental car ... more
Go to Healdsburg Forums »
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns