Healdsburg vacation rentals

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Top-rated vacation rentals in Healdsburg

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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

G$133,736 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.

Mar 1 – 8

G$41,180 GYD 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

Oct 7 – 14

G$39,404 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

Aug 5 – 12

G$66,194 GYD 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

Jan 28 – Feb 4

G$52,460 GYD 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.

Jul 24 – 31

G$25,119 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.

Sep 23 – 30

G$157,096 GYD per night

Guest favorite

Home in Healdsburg

4.98 out of 5 average rating, 395 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 4 – 11

G$98,861 GYD 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.

Mar 10 – 17

G$94,837 GYD 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.

Jan 13 – 20

G$33,239 GYD 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

Jul 9 – 16

G$42,290 GYD 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.

Nov 30 – Dec 7

G$91,394 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, 526 reviews

Healdsburg Garden House

Mar 13 – 20

G$47,616 GYD per night

Guest favorite

Home in Healdsburg

4.91 out of 5 average rating, 125 reviews

Dry Creek w/Hot Tub, Bocce, Vineyard Views

Jan 18 – 25

G$97,433 GYD per night

Guest favorite

Home in Healdsburg

4.92 out of 5 average rating, 236 reviews

The Wine Ranch

Mar 15 – 22

G$88,895 GYD per night

Superhost

Home in Healdsburg

4.89 out of 5 average rating, 294 reviews

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

Aug 28 – Sep 4

G$92,417 GYD per night

Guest favorite

Home in Windsor

4.96 out of 5 average rating, 378 reviews

Winelight Vineyard Home With Spa

Jun 26 – Jul 3

G$45,865 GYD per night

Guest favorite

Home in Sonoma

4.95 out of 5 average rating, 396 reviews

Zen House on 15 acres

Aug 22 – 29

G$126,563 GYD per night

Superhost

Home in Healdsburg

4.81 out of 5 average rating, 124 reviews

Spectacular Vineyard View!! SPA, Close to Plaza!

Oct 30 – Nov 6

G$115,955 GYD per night

Guest favorite

Home in Cazadero

4.95 out of 5 average rating, 117 reviews

Ranch Stay for 2

Jan 28 – Feb 4

G$27,380 GYD 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

Sep 18 – 25

G$61,856 GYD per night

Guest favorite

Cottage in Cloverdale

4.97 out of 5 average rating, 113 reviews

Asti Ridge Ranch - Private One Bedroom Cottage

May 9 – 16

G$35,321 GYD per night

Superhost

Cottage in Sebastopol

4.91 out of 5 average rating, 209 reviews

Stunning Sauna Cottage Retreat on Private Vineyard

Feb 18 – 25

G$60,543 GYD per night

Guest favorite

Cottage in Sebastopol

4.99 out of 5 average rating, 158 reviews

Designer Wine Country Cottage in Perfect Location

Aug 29 – Sep 5

G$71,520 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!❤

Jun 24 – Jul 1

G$133,693 GYD per night

Guest favorite

Cottage in Sonoma

4.99 out of 5 average rating, 145 reviews

Modern Farmhouse on Vineyard w Deck + Bocce Court

Mar 10 – 17

G$88,524 GYD per night

Guest favorite

Cottage in Windsor

5.0 out of 5 average rating, 120 reviews

Vineyard Cozy Cottage & Hot Tub

Nov 3 – 10

G$48,337 GYD per night

Guest favorite

Cottage in Forestville

4.94 out of 5 average rating, 408 reviews

Cosmo Beach River-front Sanctuary

Sep 18 – 25

G$106,358 GYD 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

G$237,035 GYD per night

Guest favorite

Guesthouse in Sebastopol

4.93 out of 5 average rating, 678 reviews

Sun Drenched Flat

Oct 15 – 22

G$28,707 GYD per night

Guest favorite

Guest suite in Forestville

4.97 out of 5 average rating, 158 reviews

Forest Gem: peaceful retreat hot tub and firepit

Jun 5 – 12

G$32,151 GYD per night

Guest favorite

Guesthouse in Healdsburg

4.99 out of 5 average rating, 209 reviews

Bunkhouse at Side Road Farm

Jul 10 – 17

G$51,673 GYD 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!**

Aug 24 – 31

G$32,838 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 17 – 24

G$107,007 GYD per night

Guest favorite

Guesthouse in Sebastopol

4.96 out of 5 average rating, 300 reviews

Arbor View

Jul 5 – 12

G$25,340 GYD per night

Guest favorite

Apartment in Santa Rosa

4.97 out of 5 average rating, 762 reviews

Private Getaway in West Santa Rosa

Feb 24 – Mar 3

G$20,581 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$16,719 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

Villas

Cabins

Houses

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 Windsor

Home in Sonoma

Home in Healdsburg

Home in Cazadero

Healdsburg cottage rentals

Cottage in Healdsburg

Cottage in Cloverdale

Cottage in Sebastopol

Cottage in Sebastopol

Cottage in Healdsburg

Cottage in Sonoma

Cottage in Windsor

Cottage in Forestville

Other great vacation rentals in Healdsburg

Cabin in Healdsburg

Guesthouse in Sebastopol

Guest suite in Forestville

Guesthouse in Healdsburg

Apartment in Sebastopol

Guesthouse in Healdsburg

Guesthouse in Sebastopol

Apartment in Santa Rosa

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