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 Sebastopol

4.93 out of 5 average rating, 674 reviews

Sun Drenched Flat

Put up the burnt-orange parasol and settle down with book on the patio while the barbecue heats up. Sitting above a garage in a serene, walkable neighborhood, this sunlit retreat's beachy cream painted paneling gives it a chilled, refined vibe. Check out all that Sebastopol has to offer at: visitsebastopolnow.come This second story house is a very desirable space, located close to town, still being set on a very beautiful street in an friendly established older neighborhood. It is nestled between other structures on the property. One being a "Tiny House" that is right next door, my home sits behind the flat. The house has a full kitchen with all the utensils and necessary cooking items, pots pans etc. Large toaster oven that will even fit your frozen pizza. There is a space in front with some Adirondack chairs and BBQ if you want to relax outside. The house has its own separate entrance off the driveway. My house is in back of the flat, I may or may not see you, but I am available for any questions at any time. You will more than likely be greeted by our white cat with orange tips (named White Boy). If he gets a chance, Charlie our very exuberant Golden Doodle will give you a warm excited welcome. Located just 1 mile from the heart of the sweet town of Sebastopol, this area is a handy stepping off point to explore nearby wineries, scenic beaches, and shopping and restaurants at redwoods. A very nice mile walk to town or a five minute drive. There is a flight of stairs that you climb to get to the Flat space, it does not have wheelchair access. There are cats on the property, but they do not go inside the flat. Our Goldendoodle is extremely friendly. The leather couch folds flat into a double bed for accommodating two more guests. Access to the bathroom is through the bedroom however. There is no dedicated parking, however the street parking directly across from the flat, just up from, but not in front of the three mailboxes is usually always open.

Jul 1 – 8

$120 per night
Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 177 reviews

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)

Oct 17 – 24

$630 per night
Guest favorite

Home in Healdsburg

4.96 out of 5 average rating, 429 reviews

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.

Mar 26 – Apr 2

$172 per night

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

Guest favorite

Home in Healdsburg

4.93 out of 5 average rating, 522 reviews

Healdsburg Garden House

Nov 25 – Dec 2

$197 per night
Superhost

Home in Healdsburg

4.89 out of 5 average rating, 292 reviews

Peaceful location, hot tub, fire pit, game room!

Apr 20 – 27

$355 per night
Guest favorite

Home in Graton

5.0 out of 5 average rating, 556 reviews

Eco Luxury Private Sanctuary / The Farmhouse Oasis

Oct 16 – 23

$406 per night
Guest favorite

Home in Healdsburg

4.92 out of 5 average rating, 234 reviews

The Wine Ranch

Nov 5 – 12

$370 per night
Guest favorite

Home in Sonoma

4.95 out of 5 average rating, 394 reviews

Zen House on 15 acres

Jul 26 – Aug 2

$720 per night
Guest favorite

Home in Cazadero

4.95 out of 5 average rating, 114 reviews

Ranch Stay for 2

Jan 19 – 26

$113 per night
Guest favorite

Home in Sebastopol

4.96 out of 5 average rating, 362 reviews

Sebastopol Guest House

Jun 6 – 13

$121 per night
Guest favorite

Home in Windsor

4.99 out of 5 average rating, 101 reviews

Gorgeous Victorian in the HEART of Windsor

Sep 6 – 13

$394 per night
Guest favorite

Home in Windsor

4.96 out of 5 average rating, 377 reviews

Winelight Vineyard Home With Spa

Dec 26 – Jan 2

$240 per night
Guest favorite

Home in Windsor

4.99 out of 5 average rating, 139 reviews

Luxury Wine Country Estate with pool & hot tub

Sep 8 – 15

$551 per night
Guest favorite

Home in Sonoma

4.99 out of 5 average rating, 115 reviews

Easy elegance in this wine country home

Jul 24 – 31

$708 per night
Guest favorite

Home in Forestville

4.99 out of 5 average rating, 251 reviews

Somms Rest Designed Curated Peaceful

Apr 14 – 21

$248 per night

Healdsburg cottage rentals

Guest favorite

Cottage in Healdsburg

5.0 out of 5 average rating, 157 reviews

Bee Haven Cottage

Jul 25 – Aug 1

$258 per night
Superhost

Cottage in Sebastopol

4.92 out of 5 average rating, 200 reviews

Stunning Sauna Cottage Retreat on Private Vineyard

Dec 31 – Jan 7

$252 per night
Guest favorite

Cottage in Cloverdale

4.97 out of 5 average rating, 112 reviews

Asti Ridge Ranch - Private One Bedroom Cottage

Apr 29 – May 6

$146 per night
Guest favorite

Cottage in Sebastopol

4.99 out of 5 average rating, 156 reviews

Designer Wine Country Cottage in Perfect Location

Oct 31 – Nov 7

$265 per night
Guest favorite

Cottage in Windsor

5.0 out of 5 average rating, 117 reviews

Vineyard Cozy Cottage & Hot Tub

Dec 20 – 27

$202 per night
Guest favorite

Cottage in Sonoma

4.99 out of 5 average rating, 140 reviews

Modern Farmhouse on Vineyard w Deck + Bocce Court

Feb 3 – 10

$326 per night
Guest favorite

Cottage in Healdsburg

4.95 out of 5 average rating, 108 reviews

❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤

Jun 29 – Jul 6

$718 per night
Guest favorite

Cottage in Forestville

4.94 out of 5 average rating, 406 reviews

Cosmo Beach River-front Sanctuary

Aug 2 – 9

$492 per night
Superhost

Cottage in Forestville

4.92 out of 5 average rating, 303 reviews

Nestled in Nature

May 29 – Jun 5

$281 per night
Guest favorite

Cottage in Jenner

4.99 out of 5 average rating, 350 reviews

Riverfront Serenity on the Sonoma Coast

Nov 12 – 19

$274 per night
Guest favorite

Cottage in Occidental

4.96 out of 5 average rating, 557 reviews

The Perch

Apr 3 – 10

$145 per night
Guest favorite

Cottage in Sebastopol

4.98 out of 5 average rating, 113 reviews

Unique Wine Country~Garden Gem

Jun 14 – 21

$325 per night

Other great vacation rentals in Healdsburg

Guest favorite

Guest suite in Forestville

4.97 out of 5 average rating, 152 reviews

Forest Gem: peaceful retreat hot tub and firepit

May 15 – 22

$134 per night
Guest favorite

Loft in Windsor

4.81 out of 5 average rating, 499 reviews

The Loft Under The Oaks

Nov 21 – 28

$120 per night
Guest favorite

Guesthouse in Santa Rosa

4.89 out of 5 average rating, 674 reviews

Wine Country guest house

Sep 28 – Oct 5

$94 per night
Guest favorite

Guesthouse in Healdsburg

4.94 out of 5 average rating, 285 reviews

Th Roost - Sun Room

Mar 3 – 10

$261 per night
Guest favorite

Guesthouse in Healdsburg

4.99 out of 5 average rating, 208 reviews

Bunkhouse at Side Road Farm

Jul 17 – 24

$220 per night
Guest favorite

Apartment in Sebastopol

4.99 out of 5 average rating, 601 reviews

Amy's Local BNB - walk to town **and hot tub!**

Aug 21 – 28

$134 per night
Guest favorite

Guesthouse in Healdsburg

4.93 out of 5 average rating, 299 reviews

Healdsburg Cottage-Workspace, Walk to Plaza

Oct 16 – 23

$282 per night
Guest favorite

Guesthouse in Sebastopol

4.9 out of 5 average rating, 1107 reviews

Lemon Moon Cottage

Feb 9 – 14

$129 per night
Guest favorite

Apartment in Santa Rosa

4.97 out of 5 average rating, 755 reviews

Private Getaway in West Santa Rosa

Nov 17 – 24

$86 per night
Guest favorite

Guest suite in Sebastopol

5.0 out of 5 average rating, 344 reviews

#1 Host In CA: Modern. Serene. Spectacular Views!

Mar 3 – 10

$286 per night
Guest favorite

Guesthouse in Sebastopol

4.96 out of 5 average rating, 289 reviews

Arbor View

Jun 18 – 25

$106 per night
Guest favorite

Guesthouse in Healdsburg

4.96 out of 5 average rating, 101 reviews

Dog Friendly Healdsburg / Dry Creek Valley Cottage

Mar 9 – 16

$446 per night

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 10 homes with self check-in, over 30 homes with a bbq area, 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