Healdsburg vacation rentals

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Top-rated vacation rentals in Healdsburg

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Guest favorite

Guesthouse in Sebastopol

4.93 out of 5 average rating, 678 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.

Mar 2 – 9

R2,633 ZAR 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)

Sep 24 – Oct 1

R12,263 ZAR 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.

Aug 29 – Sep 5

R3,777 ZAR per night

Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 249 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 25 – Oct 2

R3,614 ZAR 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

Nov 6 – 13

R5,774 ZAR per night

Guest favorite

Home in Healdsburg

4.96 out of 5 average rating, 146 reviews

Wine Country Cottage Walkable to River or Downtown

Centrally located retreat 5 blocks from downtown, Russian River and 3 blocks from at least 9 wineries. Living room fully opens to private deck w/BBQ, outdoor kitchen, dining space and fire place Gourmet equipped kitchen with many cooking amenities to enjoy wine and a great meal in the garden patio or BBQ outside and relax by the fire Luxury bathroom with heated towel rack and bidet Two bedrooms with one converting into a home office. Lots of extra amenities and thoughtful comfortable touches

Dec 9 – 16

R4,955 ZAR per night

Guest favorite

Guest suite in Windsor

4.98 out of 5 average rating, 357 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

R2,408 ZAR 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.

Sep 24 – Oct 1

R14,408 ZAR per night

Superhost

Villa in Healdsburg

4.94 out of 5 average rating, 112 reviews

Hilltop Vista Villa

Set on an Acre by Fitch Mountain Park and Open Space Preserve, Hilltop Vista Villa offers a quiet private setting, spectacular views of world class vineyards, private access to hiking trails and proximity to the Russian River beach. This inviting single level retreat has an open floor plan with lots of sunshine. The open kitchen features stainless steel appliances, custom cabinetry, and a granite topped island. The Master Suite includes a custom soaking tub.

Nov 4 – 11

R8,698 ZAR per night

Superhost

Townhouse in Healdsburg

4.83 out of 5 average rating, 542 reviews

B - Wine Country Getaway

Great Townhouse 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.

Feb 8 – 15

R3,049 ZAR per night

Guest favorite

Guest suite in Healdsburg

4.92 out of 5 average rating, 411 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

Oct 3 – 10

R3,879 ZAR per night

Guest favorite

Cottage in Healdsburg

5.0 out of 5 average rating, 242 reviews

Luxurious, Private, Healdsburg Guest Cottage

1083 Guest House is a Healdsburg find; comfortable luxury in a spacious private cottage with terrific amenities within walking distance of four-star restaurants, wineries, fabulous boutique shopping, and the Russian River. Your secluded cottage is nestled in the trees with views of a wooded area and is the perfect destination for your personal romantic getaway to enjoy all that the Wine Country has to offer.

Mar 25 – Apr 1

R8,073 ZAR 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, 526 reviews

Healdsburg Garden House

Mar 23 – 30

R4,367 ZAR per night

Guest favorite

Home in Healdsburg

4.98 out of 5 average rating, 395 reviews

Vineyard Modern Barn House - Dry Creek Valley

Jan 5 – 12

R9,067 ZAR per night

Guest favorite

Home in Healdsburg

4.91 out of 5 average rating, 126 reviews

Dry Creek w/Hot Tub, Bocce, Vineyard Views

Sep 9 – 16

R8,506 ZAR per night

Guest favorite

Home in Healdsburg

4.92 out of 5 average rating, 236 reviews

The Wine Ranch

Oct 12 – 19

R8,926 ZAR per night

Superhost

Home in Healdsburg

4.89 out of 5 average rating, 294 reviews

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

Nov 23 – 30

R8,476 ZAR per night

Guest favorite

Home in Sonoma

4.95 out of 5 average rating, 397 reviews

Zen House on 15 acres

Sep 7 – 14

R14,701 ZAR per night

Guest favorite

Home in Cazadero

4.95 out of 5 average rating, 117 reviews

Ranch Stay for 2

Feb 6 – 13

R2,511 ZAR per night

Guest favorite

Home in Graton

5.0 out of 5 average rating, 561 reviews

Eco Luxury Private Sanctuary / The Farmhouse Oasis

Nov 3 – 10

R8,958 ZAR per night

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Healdsburg cottage rentals

Guest favorite

Cottage in Healdsburg

5.0 out of 5 average rating, 158 reviews

Bee Haven Cottage

Aug 20 – 27

R5,673 ZAR per night

Guest favorite

Cottage in Cloverdale

4.97 out of 5 average rating, 113 reviews

Asti Ridge Ranch - Private One Bedroom Cottage

May 10 – 17

R3,240 ZAR per night

Superhost

Cottage in Sebastopol

4.91 out of 5 average rating, 209 reviews

Stunning Sauna Cottage Retreat on Private Vineyard

Jan 15 – 22

R5,553 ZAR per night

Guest favorite

Cottage in Sebastopol

4.99 out of 5 average rating, 158 reviews

Designer Wine Country Cottage in Perfect Location

Dec 26 – Jan 2

R5,921 ZAR per night

Guest favorite

Cottage in Healdsburg

4.96 out of 5 average rating, 112 reviews

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

Jun 24 – Jul 1

R12,262 ZAR per night

Guest favorite

Cottage in Windsor

5.0 out of 5 average rating, 120 reviews

Vineyard Cozy Cottage & Hot Tub

Feb 13 – 20

R4,970 ZAR per night

Guest favorite

Cottage in Sonoma

4.99 out of 5 average rating, 145 reviews

Modern Farmhouse on Vineyard w Deck + Bocce Court

Aug 12 – 19

R9,550 ZAR per night

Guest favorite

Cottage in Forestville

4.94 out of 5 average rating, 408 reviews

Cosmo Beach River-front Sanctuary

Aug 7 – 14

R11,442 ZAR per night

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Other great vacation rentals in Healdsburg

Guest favorite

Cabin in Healdsburg

4.95 out of 5 average rating, 139 reviews

Starlight Grove-a redwood retreat (fiber internet)

Oct 17 – 24

R21,743 ZAR per night

Guest favorite

Guesthouse in Santa Rosa

4.89 out of 5 average rating, 675 reviews

Wine Country guest house

Oct 27 – Nov 3

R2,090 ZAR per night

Guest favorite

Apartment in Sebastopol

4.99 out of 5 average rating, 607 reviews

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

Oct 4 – 11

R2,986 ZAR per night

Guest favorite

Guesthouse in Healdsburg

4.96 out of 5 average rating, 101 reviews

Dog Friendly Healdsburg / Dry Creek Valley Cottage

Mar 18 – 25

R9,814 ZAR per night

Guest favorite

Guesthouse in Healdsburg

4.99 out of 5 average rating, 209 reviews

Bunkhouse at Side Road Farm

Aug 21 – 28

R5,702 ZAR per night

Guest favorite

Guesthouse in Sebastopol

4.96 out of 5 average rating, 300 reviews

Arbor View

Jul 7 – 14

R2,324 ZAR per night

Guest favorite

Apartment in Santa Rosa

4.97 out of 5 average rating, 762 reviews

Private Getaway in West Santa Rosa

Jan 13 – 20

R1,888 ZAR per night

Guest favorite

Guesthouse in Healdsburg

4.93 out of 5 average rating, 299 reviews

Healdsburg Cottage-Workspace, Walk to Plaza

Feb 11 – 18

R6,212 ZAR 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
R1,533 ZAR 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

Villas

Cabins

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 Healdsburg

Home in Healdsburg

Home in Sonoma

Home in Cazadero

Home in Graton

Healdsburg cottage rentals

Cottage in Healdsburg

Cottage in Cloverdale

Cottage in Sebastopol

Cottage in Sebastopol

Cottage in Healdsburg

Cottage in Windsor

Cottage in Sonoma

Cottage in Forestville

Other great vacation rentals in Healdsburg

Cabin in Healdsburg

Guesthouse in Santa Rosa

Apartment in Sebastopol

Guesthouse in Healdsburg

Guesthouse in Healdsburg

Guesthouse in Sebastopol

Apartment 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?

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