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.

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Guest favorite

Guesthouse in Sebastopol

4.93 out of 5 average rating, 681 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.

Apr 14 – 21

G$28,638 GYD 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)

Jul 9 – 16

G$109,622 GYD per night

Guest favorite

Home in Healdsburg

4.96 out of 5 average rating, 430 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.

Sep 3 – 10

G$41,081 GYD per night

Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 250 reviews

Alexander Valley: Wine Lover and Cycling Paradise

The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N

Sep 6 – 13

G$39,309 GYD per night

Guest favorite

Farm stay in Healdsburg

4.97 out of 5 average rating, 475 reviews

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

Oct 12 – 19

G$66,035 GYD per night

Guest favorite

Apartment in Sebastopol

4.99 out of 5 average rating, 608 reviews

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

Amy’s Local BNB is nestled among huge fir trees in a quiet neighborhood a short walk from downtown Sebastopol. This sunny contemporary gem focuses on our commitment to local and sustainably sourced food, wine, and crafts. With a full kitchen, you can enjoy the comforts of a meal cooked “at home” from the local farmer’s market, or walk to superb local eateries. We will share maps to our favorite swimming hole on the Russian River or to ocean beaches, or introduce you to excellent local vintners.

Oct 11 – 18

G$33,188 GYD per night

Guest favorite

Guest suite in Windsor

4.98 out of 5 average rating, 361 reviews

Private Entrance Suite in Heart of Wine Country

Situated in an upscale neighborhood, this exquisite guest suite boasts a private entrance on a safe, quiet cul-de-sac in the heart of the wine country. The en-suite is perfect for a romantic getaway, comfortable for an infant or small child, and ideal for the business traveler. We are 5 miles from Healdsburg and 3 from the Sonoma Co. Airport. Three parks within 4 miles encompass over 20 miles of hiking/biking. The Russian River, Redwoods, and Sonoma Coast are only a short, panoramic drive away.

Aug 13 – 20

G$27,230 GYD per night

Guest favorite

Home in Healdsburg

4.97 out of 5 average rating, 149 reviews

Secluded Healdsburg Sanctuary on 10 Private Acres

This stunning, modern home sits on a picturesque 10-acre property, complete with a thriving vineyard that provides a serene and secluded backdrop for your getaway. As you enter the home you'll be struck by its elegant and refined design and large picture windows that look out on breathtaking vistas of vine, olive & oak dotted hills. Whether you are seeking a romantic getaway, a family vacation or a peaceful respite from city life, this exceptional retreat has everything you need & more.

Aug 11 – 18

G$156,718 GYD per night

Guest favorite

Home in Healdsburg

4.98 out of 5 average rating, 397 reviews

Vineyard Modern Barn House - Dry Creek Valley

Stylish house on a 9 acre vineyard. Beautifully crafted, the property features high end furnishings, professionally laundered/ironed sheets, original art, and 2 master bedroom suites separated by a great room w/full kitchen. Close-in location up a gated road, 5 min. to the Plaza. Amazing view from the 45 foot covered porch overlooking vineyards and Dry Creek Valley. Perfect for two couples; not suitable for infants or children under 8, max 2 daytime guests. No parties or pets allowed.

Jan 2 – 9

G$98,623 GYD per night

Superhost

Home in Healdsburg

4.81 out of 5 average rating, 424 reviews

C - Wineries/breweries seconds away

Great location for a wine country getaway! Please use the Airbnb app for self check-in instructions! The owner is severely allergic to animals, so please do not request or bring any animal with you. We have an automated backup generator for loss of power issues! Full kitchen, Outdoor patio, BBQ, Fire pit (propane tank included but not fuel), Two bikes included in stay. California King Tempurpedic bed. Laundry room, Fully renovated bathroom.

Jan 14 – 21

G$33,526 GYD per night

Guest favorite

Guest suite in Forestville

4.97 out of 5 average rating, 159 reviews

Forest Gem: peaceful retreat hot tub and firepit

Kick back and relax in this quiet cabin in the woods. This stylish guest suite was designed to provide a regenerative retreat in nature. Enjoy the magnificent surroundings, or work remotely in a peaceful environment. Unwind in the hot tub in the middle of the trees or enjoy a cozy evening by the fire pit gazing at the stars. ** We invite you to read the full description and house rules to ensure a 5-star experience for all **

Sep 29 – Oct 6

G$32,073 GYD per night

Guest favorite

Guest suite in Healdsburg

4.92 out of 5 average rating, 412 reviews

Pony Ranch Vineyard Estate with Pool

Guest House with private entrance on gorgeous gated Vineyard Estate. Overlooks pool and vineyards with views to Mount St. Helena. Gas fireplace, refrigerator, microwave, Keurig coffee maker, queen bed. Toilet and sink separate from shower. 8 minutes to the Healdsburg Plaza. Less than a mile from 3 wineries, very close to dozens more. Agricultural Education Programs available. Sonoma County TOT Certificate 1362N

Jun 26 – Jul 3

G$42,188 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Healdsburg vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Healdsburg's top sights

Healdsburg Plaza47 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

Campo Fina60 locals recommend

Other great vacation rentals in Healdsburg

Guest favorite

Home in Healdsburg

4.93 out of 5 average rating, 528 reviews

Healdsburg Garden House

Dec 8 – 15

G$47,502 GYD per night

Guest favorite

Home in Healdsburg

4.91 out of 5 average rating, 127 reviews

Dry Creek w/Hot Tub, Bocce, Vineyard Views

Feb 28 – Mar 7

G$97,198 GYD per night

Superhost

Home in Healdsburg

4.88 out of 5 average rating, 138 reviews

Modern Home in Hburg Wine Country

Mar 30 – Apr 6

G$143,293 GYD per night

Guest favorite

Home in Sebastopol

4.96 out of 5 average rating, 367 reviews

Sebastopol Guest House

Jul 4 – 11

G$29,844 GYD per night

Guest favorite

Home in Cazadero

4.95 out of 5 average rating, 118 reviews

Ranch Stay for 2

Oct 25 – Nov 1

G$27,314 GYD per night

Guest favorite

Home in Windsor

4.96 out of 5 average rating, 380 reviews

Winelight Vineyard Home With Spa

Oct 6 – 13

G$45,755 GYD per night

Guest favorite

Home in Healdsburg

4.92 out of 5 average rating, 237 reviews

The Wine Ranch

Jul 31 – Aug 7

G$97,093 GYD per night

Guest favorite

Home in Sonoma

4.97 out of 5 average rating, 452 reviews

The Loft at Palmer-Close to it all!

Jul 23 – 30

G$28,817 GYD per night

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Healdsburg cottage rentals

Guest favorite

Cottage in Healdsburg

5.0 out of 5 average rating, 160 reviews

Bee Haven Cottage

Oct 8 – 15

G$61,707 GYD per night

Superhost

Cottage in Sebastopol

4.91 out of 5 average rating, 211 reviews

Stunning Sauna Cottage Retreat on Private Vineyard

Mar 26 – Apr 2

G$60,397 GYD per night

Guest favorite

Cottage in Sebastopol

4.99 out of 5 average rating, 159 reviews

Designer Wine Country Cottage in Perfect Location

Dec 19 – 26

G$60,856 GYD per night

Guest favorite

Cottage in Cloverdale

4.97 out of 5 average rating, 113 reviews

Asti Ridge Ranch - Private One Bedroom Cottage

Sep 8 – 15

G$44,439 GYD per night

Guest favorite

Cottage in Healdsburg

4.96 out of 5 average rating, 112 reviews

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

Aug 28 – Sep 4

G$118,195 GYD per night

Guest favorite

Cottage in Windsor

5.0 out of 5 average rating, 121 reviews

Vineyard Cozy Cottage & Hot Tub

Dec 22 – 29

G$48,527 GYD per night

Guest favorite

Cottage in Sonoma

4.99 out of 5 average rating, 147 reviews

Modern Farmhouse on Vineyard w Deck + Bocce Court

Apr 9 – 16

G$94,737 GYD per night

Guest favorite

Cottage in Jenner

4.99 out of 5 average rating, 358 reviews

Riverfront Serenity on the Sonoma Coast

Feb 5 – 12

G$64,702 GYD per night

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Other great vacation rentals in Healdsburg

Superhost

Villa in Healdsburg

4.94 out of 5 average rating, 113 reviews

Hilltop Vista Villa

Jan 26 – Feb 2

G$94,575 GYD per night

Guest favorite

Apartment in Santa Rosa

4.97 out of 5 average rating, 763 reviews

Private Getaway in West Santa Rosa

Jan 23 – 30

G$20,531 GYD per night

Guest favorite

Guesthouse in Sebastopol

4.96 out of 5 average rating, 301 reviews

Arbor View

Jul 14 – 21

G$25,279 GYD per night

Guest favorite

Guesthouse in Healdsburg

4.93 out of 5 average rating, 299 reviews

Healdsburg Cottage-Workspace, Walk to Plaza

Jan 9 – 16

G$46,393 GYD per night

Guest favorite

Guesthouse in Sebastopol

4.98 out of 5 average rating, 431 reviews

Modern Bungalow Downtown Sebastopol

Jul 23 – 30

G$24,043 GYD per night

Guest favorite

Guesthouse in Healdsburg

4.96 out of 5 average rating, 101 reviews

Dog Friendly Healdsburg / Dry Creek Valley Cottage

Mar 23 – 30

G$106,750 GYD per night

Guest favorite

Guesthouse in Santa Rosa

4.89 out of 5 average rating, 675 reviews

Wine Country guest house

Dec 15 – 22

G$22,456 GYD per night

Guest favorite

Guesthouse in Healdsburg

4.99 out of 5 average rating, 209 reviews

Bunkhouse at Side Road Farm

Jun 30 – Jul 7

G$55,695 GYD per night

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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
4.3K reviews
Nightly prices starting at
G$16,679 GYD 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 wifi?
Absolutely! We offer over 50 house rentals with wifi in Healdsburg. Enjoy a tailored experience with all the comforts you desire.
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.

Healdsburg vacation rentals

Top-rated vacation rentals in Healdsburg

Vacation rentals for every style

Houses

Cabins

Villas

Popular amenities for Healdsburg vacation rentals

Stay near Healdsburg's top sights

Other great vacation rentals in Healdsburg

Home in Healdsburg

Home in Healdsburg

Home in Healdsburg

Home in Sebastopol

Home in Cazadero

Home in Windsor

Home in Healdsburg

Home in Sonoma

Healdsburg cottage rentals

Cottage in Healdsburg

Cottage in Sebastopol

Cottage in Sebastopol

Cottage in Cloverdale

Cottage in Healdsburg

Cottage in Windsor

Cottage in Sonoma

Cottage in Jenner

Other great vacation rentals in Healdsburg

Villa in Healdsburg

Apartment in Santa Rosa

Guesthouse in Sebastopol

Guesthouse in Healdsburg

Guesthouse in Sebastopol

Guesthouse in Healdsburg

Guesthouse in Santa Rosa

Guesthouse in Healdsburg

Quick stats about vacation rentals in Healdsburg

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Healdsburg?

Are there pet-friendly vacation rentals in Healdsburg?

Are there Healdsburg vacation rentals on Airbnb with pools?

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

Are there family-friendly vacation rentals in Healdsburg?

Do house rentals in Healdsburg have wifi?

Do house rentals in Healdsburg have a bbq area?

Do house rentals in Healdsburg have self check-in?

Destinations to explore