Healdsburg vacation rentals

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Top-rated vacation rentals in Healdsburg

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Healdsburg
Healdsburg Contemporary Cottage With Lush Backyard Patio
Stay in shape in the fully equipped Pilates studio, Afterwards, freshen up in the skylighted shower room with heated stone floor. Later, enjoy a glass of wine and a good book in the outdoor lounge and dine alfresco in the landscaped garden. The perfect home away from home. Makes this your personal sanctuary wether you are staying for the weekend or for the whole month while looking for the perfect home to buy. Well appointed, decorated with international contemporary art with just enough touches that take you beyond the hotel luxury suite. A great modern getaway with Garden, al fresco dining with BBQ, garden lounge area and fully equipped Pilates Studio. Park right in front of your guest house with private gated entry to your personal cottage. I am happy to help you plan your Healdsburg and Wine country excursions. From restaurants and wineries along with the perfect biking routes, top classical dressage lessons on Lusitanos or private Art Studio Tour, Pilates training at the on site studio, massage in the Guest house, Culinary Tour, Farmers Market to Picnic at Music on the Square on Tuesdays.... Head out for an easy stroll to downtown and the Plaza area, with boutiques, galleries, and antique shops to browse. Stock up at the farmers' market, sample local vintages in wine-tasting rooms, and dine at a wide choice of chic restaurants. Within easy walking distance to downtown Restaurants, Wine Tasting Rooms, Galleries, Antique Shops, Spas, Boutiques and Farmers Market. Healdsburg Contemporary Cottages is registered with the City of Healdsburg and is collecting TOT Taxes of 16% for the City of Healdsburg which are included in the pricing. The Business License Number is: (PHONE NUMBER HIDDEN)
Apr 10 – 17
$455 per night
4.98 out of 5 average rating, 178 reviews
Guest favorite
Home in Healdsburg
Dry Creek Valley Cottage
Enjoy your stay in beautiful Dry Creek Valley, a pastoral rural setting surrounded by vineyards and local wineries, minutes from Healdsburg's historic quaint downtown plaza. The cottage is 480 square feet with big windows, high ceilings and its own private entrance. There is parking right in front. It has kitchen amenities (coffee and tea pot, mini refrigerator, toaster and microwave), living room and bathroom with a mosaic tile shower. Right across the way you can take a lovely walk or run alongside the vineyards or you can rent a bike to explore the beauty of the valley. If you enjoy hiking, seasonal kayaking or canoeing there are opportunities all around us to explore as well. Our property has multiple fruit trees and we will be happy to share whatever bounty is in season when you arrive. The water here is also clean spring fed and very tasty and the sky at night is full of stars! You can enjoy sitting in the front yard which is bordered by a dozen Redwood trees or you can picnic in our big back yard among the fruit trees. We also have 2 female dogs who are quite friendly if you'd like to meet them. We would be happy to welcome you to Sonoma County and insure that your stay here is enjoyable.
Dec 3 – 10
$172 per night
4.96 out of 5 average rating, 428 reviews
Guest favorite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile in Healdsburg includes equipped kitchen. Pick up breakfast needs before arriving. House truth: Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. It can be disruptive to sleep (or not, some say it isn't a bother). LOFT AVAILABLE BUT TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. TOT #3294N
Jan 10 – 17
$263 per night
4.97 out of 5 average rating, 467 reviews

Popular amenities for Healdsburg vacation rentals

Stay near Healdsburg's top sights

Healdsburg Plaza47 locals recommend
Healdsburg Veterans Memorial Beach5 locals recommend
Bravas Bar de Tapas68 locals recommend
Willi's | Seafood & Raw Bar76 locals recommend
Big John's Market43 locals recommend
Healdsburg Bar & Grill24 locals recommend

Healdsburg home rentals

Superhost
Home in Healdsburg
C - Wineries/breweries seconds away
Aug 1 – 8
$156 per night
4.81 out of 5 average rating, 416 reviews
Guest favorite
Home in Healdsburg
Dry Creek w/Hot Tub, Bocce, Vineyard Views
Nov 6 – 13
$405 per night
4.91 out of 5 average rating, 123 reviews
Superhost
Home in Healdsburg
Peaceful location, hot tub, fire pit, game room!
Nov 2 – 9
$384 per night
4.89 out of 5 average rating, 292 reviews
Guest favorite
Home in Healdsburg
The Wine Ranch
Apr 3 – 10
$411 per night
4.92 out of 5 average rating, 234 reviews
Guest favorite
Home in Sonoma
Zen House on 15 acres
Nov 10 – 17
$386 per night
4.94 out of 5 average rating, 394 reviews
Guest favorite
Home in Windsor
Winelight Vineyard Home With Spa
Dec 5 – 12
$191 per night
4.96 out of 5 average rating, 376 reviews
Guest favorite
Home in Windsor
Gorgeous Victorian in the HEART of Windsor
Mar 20 – 27
$343 per night
4.99 out of 5 average rating, 101 reviews
Guest favorite
Home in Windsor
Luxury Wine Country Estate with pool & hot tub
Aug 12 – 19
$574 per night
4.99 out of 5 average rating, 136 reviews
Superhost
Home in Healdsburg
Spectacular Vineyard View!! SPA, Close to Plaza!
Jan 28 – Feb 4
$395 per night
4.8 out of 5 average rating, 122 reviews
Superhost
Home in Healdsburg
Redwood River House
Jan 7 – 14
$342 per night
4.81 out of 5 average rating, 102 reviews
Guest favorite
Home in Sonoma
Easy elegance in this wine country home
Aug 21 – 28
$721 per night
4.99 out of 5 average rating, 112 reviews
Guest favorite
Home in Santa Rosa
VINEYARD VIEW - Beautiful 3 bed/2 bath, Santa Rosa
Feb 27 – Mar 6
$367 per night
5.0 out of 5 average rating, 102 reviews

Healdsburg cottage rentals

Superhost
Cottage in Sebastopol
Stunning Sauna Cottage Retreat on Private Vineyard
Jan 20 – 27
$252 per night
4.92 out of 5 average rating, 198 reviews
Guest favorite
Cottage in Cloverdale
Asti Ridge Ranch - Private One Bedroom Cottage
Mar 31 – Apr 7
$143 per night
4.97 out of 5 average rating, 112 reviews
Guest favorite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
May 31 – Jun 7
$556 per night
4.95 out of 5 average rating, 106 reviews
Guest favorite
Cottage in Sebastopol
Designer Wine Country Cottage in Perfect Location
Nov 25 – Dec 2
$284 per night
4.99 out of 5 average rating, 154 reviews
Guest favorite
Cottage in Sonoma
Modern Farmhouse on Vineyard w Deck + Bocce Court
Feb 12 – 19
$400 per night
4.99 out of 5 average rating, 139 reviews
Guest favorite
Cottage in Windsor
Vineyard Cozy Cottage & Hot Tub
Feb 26 – Mar 5
$198 per night
5.0 out of 5 average rating, 116 reviews
Guest favorite
Cottage in Forestville
Cosmo Beach River-front Sanctuary
Aug 22 – 29
$492 per night
4.94 out of 5 average rating, 404 reviews
Superhost
Cottage in Forestville
Nestled in Nature
May 5 – 12
$243 per night
4.92 out of 5 average rating, 303 reviews
Guest favorite
Cottage in Jenner
Riverfront Serenity on the Sonoma Coast
Nov 15 – 22
$272 per night
4.99 out of 5 average rating, 349 reviews
Guest favorite
Cottage in Bodega Bay
Knix's Cabin at Salmon Creek
Jan 19 – 26
$195 per night
4.98 out of 5 average rating, 831 reviews
Guest favorite
Cottage in Sebastopol
Unique Wine Country~Garden Getaway!
Aug 2 – 9
$325 per night
4.98 out of 5 average rating, 112 reviews
Guest favorite
Cottage in Monte Rio
Riverfront Cottage w/ lush gardens & hot tub!
Feb 22 – Mar 1
$301 per night
4.99 out of 5 average rating, 138 reviews

Other great vacation rentals in Healdsburg

Guest favorite
Guesthouse in Healdsburg
Bunkhouse at Side Road Farm
Jun 13 – 20
$227 per night
4.99 out of 5 average rating, 208 reviews
Guest favorite
Loft in Windsor
The Loft Under The Oaks
Oct 6 – 13
$120 per night
4.81 out of 5 average rating, 499 reviews
Guest favorite
Cabin in Healdsburg
Updated Russian River Cabin (beach/river access!)
May 4 – 11
$345 per night
4.99 out of 5 average rating, 145 reviews
Guest favorite
Guest suite in Windsor
Private Entrance Suite in Heart of Wine Country
Jun 9 – 16
$107 per night
4.98 out of 5 average rating, 353 reviews
Guest favorite
Guesthouse in Healdsburg
Dog Friendly Healdsburg / Dry Creek Valley Cottage
Aug 17 – 24
$446 per night
4.96 out of 5 average rating, 101 reviews
Guest favorite
Guest suite in Sebastopol
#1 Host In CA: Modern. Serene. Spectacular Views!
Aug 4 – 11
$299 per night
5.0 out of 5 average rating, 343 reviews
Guest favorite
Guesthouse in Windsor
Sonoma county cottage. Windsor / Healdsburg
Mar 25 – Apr 1
$128 per night
4.86 out of 5 average rating, 118 reviews
Guest favorite
Guesthouse in Sebastopol
Sun Drenched Flat
Nov 4 – 11
$120 per night
4.93 out of 5 average rating, 674 reviews
Guest favorite
Guest suite in Forestville
Forest Gem: peaceful retreat in the woods
Jul 21 – 28
$150 per night
4.97 out of 5 average rating, 150 reviews
Guest favorite
Guesthouse in Santa Rosa
Wine Country guest house
Jul 8 – 15
$93 per night
4.89 out of 5 average rating, 674 reviews
Guest favorite
Home in Healdsburg
10 Acre Vineyard Cottage w/Hot Tub + Bocce Court
Dec 18 – 25
$290 per night
5.0 out of 5 average rating, 48 reviews
Guest favorite
Home in Healdsburg
Hidden Oasis ~ a Private Luxury Home in Healdsburg
Jan 12 – 19
$962 per night
4.98 out of 5 average rating, 47 reviews

Quick stats about vacation rentals in Healdsburg

Total rentals

100 properties

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

70 properties are a good fit for families

Total number of reviews

4.1K reviews

Nightly prices starting at

$80 before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Healdsburg?

    Yes! Work meets play with ease at over 60 vacation rentals in Healdsburg featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Healdsburg?

    Four-legged friends are welcome in Healdsburg. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there Healdsburg vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Healdsburg, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in house rentals in Healdsburg?

    Experience the best of Healdsburg with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly vacation rentals in Healdsburg?

    Healdsburg has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Healdsburg have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Healdsburg. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Healdsburg have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Healdsburg. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Healdsburg?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a bbq area, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Healdsburg