AllTheRooms.

Healdsburg Vacation Rentals

  1. Vacation Rental Search
  2. United States of America
  3. California
  4. Healdsburg

Our Favorite Vacation Rentals in Healdsburg

  • Downtown Suites One
     Home/Apartment
    Booking.com
    From
    $344
  • 788 Magnolia Dr Entire Property Home
     Country House
    Booking.com
    From
    $1,319
  • The Eastside - Healdsburg Family Farmhouse Home
     Country House
    Booking.com
    From
    $785
  • Hummingbird House
     Country House
    Booking.com
    From
    $363
  • Quiet Wine Country Home Home
     Country House
    Booking.com
    From
    $733
  • Rio Nido Retreat
     Country House
    Booking.com
    From
    $150
  • The Last Resort
     Country House
    Booking.com
    From
    $181
  • Melody Vineyard Cottage
     Home/Apartment
    Booking.com
    From
    $141
Show all

Check prices for these upcoming dates

Healdsburg Vacation Rentals with a Pool

  • Charming Apartment nestled in Dry Creek Valley
    Excellent2br Home/Apartment
    Airbnb
    From
    $357
  • Healdsburg Retreat with Pool and 4 minutes to town
    Excellent5br Home/Apartment
    Airbnb
    From
    $1,277
  • Stay upstairs in our family winery
    Excellent2br Home/Apartment
    Airbnb
    From
    $245
  • Visit Famous Wineries from a Country House with a Pool
    Excellent3br Home/Apartment
    Airbnb
    From
    $1,167
Show all

Healdsburg Vacation Rentals with Wi-Fi

  • The Woods Resort - A Gay Friendly Resort
    Nice19br 3-star Home/Apartment
    Booking.com
    From
    $149
  • Healdsburg Contemporary Cottage With Lush Backyard Patio
    ExcellentHome/Apartment
    Airbnb
    From
    $371
  • The Duck Farm Close to HBG Square
    Excellent3br Home/Apartment
    Airbnb
    From
    $763
  • Dry Creek Valley Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $195
Show all

Healdsburg Pet-Friendly Vacation Rentals

  • Healdsburg Garden House
    Excellent2br Home/Apartment
    Airbnb
    From
    $145
  • Beautiful Wine Country Views
    Excellent2br Home/Apartment
    Airbnb
    From
    $593
  • VineHaven
    Good3br Home/Apartment
    Airbnb
    From
    $622
  • Vineyard Views at the KC House
    Excellent4br Home/Apartment
    Airbnb
    From
    $733
Show all

Healdsburg Travel Guide

In California Wine Country is the vibrant city of Healdsburg, which is known as one of the best small towns in the United States and is home to three of the best wineries in the country. This calls for some wine tasting! Foodies will also love the fine-dining restaurants in Healdsburg too. The downtown area is perfect for a leisurely stroll, with shopping boutiques and art galleries around every corner, as well as cafés.

Things to Do in Healdsburg

One of the top places to go in Healdsburg is Ferrari-Carano Winery and Gardens. Of course, the tasting of wine is why everyone comes here but the gardens are truly stunning. Visitors can admire the tulip and daffodil displays in the spring, as well as waterfalls and foot bridges over streams. To learn more about Healdsburg, there is the Healdsburg Museum, with the building being amazing architecture from 1910.

Best Time to Visit Healdsburg

The best time to visit Healdsburg is during the spring, summer and fall months.

More+

Price and Availability in Healdsburg

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
The cheapest day to stay at a vacation rental in Healdsburg tends to be Tuesday, while the most expensive day tends to be Saturday. Vacation homes in Healdsburg tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Healdsburg is in June, while the cheapest month is in November. The most popular time to book a vacation rental in Healdsburg is in the high season in September. Healdsburg has its low season in January, when less people are visiting and the vacation home occupancy rate drops.
More+

The Weather in Healdsburg

Rainy days
69° 35°
3
74° 37°
6
84° 27°
0
91° 33°
6
86° 36°
3
93° 44°
0
103° 45°
0
104° 51°
0
103° 50°
0
98° 44°
0
91° 44°
1
91° 32°
5
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Rainy days

This climate histogram shows you the weather patterns in Healdsburg. The warmest months in Healdsburg are June and July, when temperatures reach 104 ˚F. The coolest month is November, when temperatures drop to 27 ˚F. The wettest month in Healdsburg is October with 6.04 inches of rain, while the driest month is August with 0.15 inches of rain.

More+

What Expert Travelers Think

  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
    My AnasaMy Anasa
    Visit My Anasa

  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info
    ArtMatters.Info

  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels
    Visit Coco Travels

Vacation Rentals in Healdsburg

Browse rentals from all the best providers including Airbnb, RedAwning, Priceline and many more at AllTheRooms.com. Healdsburg has 756 hotels, vacation rentals and other special places to stay, with prices to suit budget travelers, extravagant travelers and everything in between. A trip to Healdsburg can be affordable - our lowest price rental is available at $32 per night. The average price of a rental is around $612 per night.

Those needing to get some work done during their trip to Healdsburg can pick from 208 places to stay that have WiFi. We have 43 accommodations that come with breakfast included. Fitness fanatics can get a workout in during their stay by choosing from 17 accommodations that have gyms. Driving to Healdsburg? Then choose one of the 209 places to stay that comes with a parking spot included. We have 76 hotels and vacation rentals that have a pool or jacuzzi.

If you're traveling with a furry friend, then be sure to select one of the 53 pet-friendly accommodations available.

We compare vacation rentals, hotels and other bespoke accommodation types from loads of providers in Healdsburg, including 197 places to stay from Airbnb, 8 accommodations from RedAwning and 5 places to stay from Priceline

393 of the rentals in Healdsburg have been rated by previous guests. They rated 67% as excellent or good. 181 places to stay in are instantly bookable.

More+

Destinations near Healdsburg

  • Los Angeles17,898 Properties
  • Mammoth Lakes16,862 Properties
  • Big Bear Lake14,845 Properties
  • San Diego9,712 Properties
  • Palm Springs9,614 Properties
  • Big Bear City6,323 Properties
  • San Francisco6,171 Properties
  • La Quinta6,023 Properties
  • Palm Desert5,590 Properties
  • South Lake Tahoe5,256 Properties
  • Venice4,573 Properties
  • Indio4,204 Properties
  • Oceanside4,082 Properties
  • Anaheim3,716 Properties
  • Hollywood3,463 Properties
  • San Jose2,775 Properties
  • Santa Monica2,740 Properties
  • Napa2,731 Properties
  • Cathedral City2,439 Properties
  • Carlsbad2,415 Properties
  • Lake Arrowhead2,402 Properties
  • Truckee2,317 Properties
  • Santa Cruz2,288 Properties
  • Mountain View2,180 Properties
  • Sunnyvale2,094 Properties
  • Beverly Hills1,991 Properties
  • Santa Barbara1,908 Properties
  • Yosemite National Park1,874 Properties
  • Sea Ranch1,865 Properties
  • Rancho Mirage1,859 Properties
  • Santa Clara1,838 Properties
  • Olympic Valley1,772 Properties
  • Malibu1,712 Properties
  • Solana Beach1,707 Properties
  • San Clemente1,670 Properties
  • Newport Beach1,617 Properties
  • Oakland1,616 Properties
  • Huntington Beach1,570 Properties
  • Idyllwild1,525 Properties
  • Joshua Tree1,496 Properties
  • Sacramento1,448 Properties
  • Pismo Beach1,412 Properties
  • Laguna Beach1,403 Properties
  • Bermuda Dunes1,377 Properties
  • Santa Rosa1,346 Properties
  • Groveland1,332 Properties
  • Encinitas1,299 Properties
  • Ventura1,278 Properties
  • Costa Mesa1,277 Properties
  • Redding1,267 Properties
  • Oxnard1,259 Properties
  • Carmel-by-the-Sea1,246 Properties
  • Pacific Grove1,235 Properties
  • Garden Grove1,222 Properties
  • Sonoma1,218 Properties
  • Berkeley1,198 Properties
  • Arnold1,179 Properties
  • Temecula1,159 Properties
  • Carnelian Bay1,132 Properties
  • San Luis Obispo1,108 Properties
  • Monterey1,093 Properties
  • Tahoe City1,089 Properties
  • Morro Bay1,073 Properties
  • Sherman Oaks1,066 Properties
  • Oakhurst1,057 Properties
  • Desert Hot Springs1,050 Properties
  • West Hollywood1,044 Properties
  • Inglewood1,016 Properties
  • Guerneville1,014 Properties
  • Irvine1,005 Properties
  • Redwood City997 Properties
  • Daly City984 Properties
  • Bakersfield976 Properties
  • Cambria975 Properties
  • Burbank974 Properties
  • Tahoe Vista962 Properties
  • Coronado954 Properties
  • Menlo Park948 Properties
  • Orange927 Properties
  • Yucca Valley905 Properties
  • Palo Alto903 Properties
  • Fawnskin880 Properties
  • South San Francisco865 Properties
  • Fort Bragg863 Properties
  • Milpitas817 Properties
  • Windsor815 Properties
  • Chico804 Properties
  • Cupertino802 Properties
  • Woodland Hills789 Properties
  • Aptos783 Properties
  • Seaside765 Properties
  • Coachella761 Properties
  • Mill Valley754 Properties
  • Twentynine Palms736 Properties
  • Mariposa733 Properties
  • Mendocino726 Properties
  • Shaver Lake709 Properties
  • Marina del Rey704 Properties
  • Indian Wells700 Properties
  • Eureka686 Properties
  • Borrego Springs683 Properties
  • Paso Robles679 Properties
  • Escondido673 Properties
  • Avalon667 Properties
  • Fullerton652 Properties
  • Studio City648 Properties
  • Cayucos628 Properties
  • Calistoga625 Properties
  • Alameda622 Properties
  • Bass Lake621 Properties
  • Pasadena617 Properties
  • Vallejo614 Properties
  • Manhattan Beach611 Properties
  • St. Helena607 Properties
  • Three Rivers601 Properties
  • Long Beach600 Properties
  • Arcata597 Properties
  • Rancho Cucamonga592 Properties
  • Hawthorne585 Properties
  • Westminster582 Properties
  • Goleta579 Properties
  • Salinas576 Properties
  • San Rafael566 Properties
  • Del Mar566 Properties
  • Hermosa Beach561 Properties
  • Topanga549 Properties
  • San Bruno544 Properties
  • Arcadia537 Properties
  • Kings Beach533 Properties
  • Buena Park533 Properties
  • Trinidad532 Properties
  • Imperial Beach527 Properties
  • Vista526 Properties
  • Nevada City521 Properties
  • Modesto515 Properties
  • Chula Vista515 Properties
  • La Mesa514 Properties
  • El Segundo512 Properties
  • Pacifica510 Properties
  • Newport Coast501 Properties
  • Gualala499 Properties
  • Santa Ana497 Properties
  • Alhambra497 Properties
  • Crescent City494 Properties
  • Visalia493 Properties
  • Culver City491 Properties
  • Sebastopol490 Properties
  • Solvang483 Properties
  • El Cajon477 Properties
  • Ojai473 Properties
  • Burlingame472 Properties
  • Templeton472 Properties
  • Avila Beach471 Properties
  • Campbell470 Properties
  • Watsonville465 Properties
  • Murrieta463 Properties
  • June Lake459 Properties
  • Carpinteria458 Properties
  • Pacific Palisades457 Properties
  • Oceano452 Properties
  • Arroyo Grande444 Properties
  • Rancho Cordova442 Properties
  • Pebble Beach437 Properties
  • Roseville430 Properties
  • Hacienda Heights430 Properties
  • Atascadero429 Properties
  • Dana Point428 Properties
  • Capitola428 Properties
  • Carmel Valley427 Properties
  • Bodega Bay424 Properties
  • Livermore418 Properties
  • Los Gatos415 Properties
  • Julian415 Properties
  • Clovis412 Properties
  • Grass Valley412 Properties
  • Petaluma411 Properties
  • Walnut Creek409 Properties
  • Thousand Oaks400 Properties
  • Santa Maria399 Properties
  • Crestline396 Properties
  • Dublin394 Properties
  • North Hollywood389 Properties
  • Mount Shasta388 Properties
  • Los Altos386 Properties
  • Pomona384 Properties
  • Lancaster382 Properties
  • Glen Ellen381 Properties
  • Union City377 Properties
  • Seal Beach374 Properties
  • Angels Camp374 Properties
  • Playa Vista369 Properties
  • Bishop364 Properties
  • Cardiff-by-the-Sea364 Properties
  • Altadena361 Properties
  • Fallbrook360 Properties
  • Fresno358 Properties
  • Lake Forest354 Properties
  • Palmdale353 Properties
  • Newark348 Properties
  • Concord344 Properties
  • Victorville341 Properties
  • Lodi340 Properties
  • Encino337 Properties
  • Hayward333 Properties
  • Barstow331 Properties
  • Grover Beach331 Properties
  • Sausalito329 Properties
  • Merced323 Properties
  • Novato322 Properties
  • Kirkwood321 Properties
  • Marina315 Properties
  • Laguna Niguel314 Properties
  • Tarzana311 Properties
  • Davis309 Properties
  • San Marcos307 Properties
  • Corona306 Properties
  • San Carlos304 Properties
  • Chino Hills303 Properties
  • Twain Harte303 Properties
  • Running Springs303 Properties
  • Fairfield302 Properties
  • Whittier302 Properties
  • Pleasanton298 Properties
  • Castro Valley294 Properties
  • Morgan Hill294 Properties
  • Murphys290 Properties
  • Monte Rio289 Properties
  • Sonora287 Properties
  • Diamond Bar287 Properties
  • Richmond287 Properties
  • Fontana284 Properties
  • Belmont284 Properties
  • Elk Grove283 Properties
  • Tahoma280 Properties
  • San Ramon280 Properties
  • El Cerrito279 Properties
  • Mission Viejo270 Properties
  • Foster City270 Properties
  • Vacaville269 Properties
  • National City268 Properties
  • Riverside268 Properties
  • San Mateo266 Properties
  • Camarillo264 Properties
  • Redondo Beach264 Properties
  • Placerville262 Properties
  • Tustin257 Properties
  • Redlands251 Properties
  • Ramona250 Properties
  • San Leandro246 Properties
  • San Pedro246 Properties
  • Stockton246 Properties
  • Blythe242 Properties
  • Ukiah241 Properties
  • Stinson Beach237 Properties
  • Gilroy234 Properties
  • Lompoc233 Properties
  • Folsom232 Properties
  • Forestville230 Properties
  • Little River228 Properties
  • Glendale226 Properties
  • Port Hueneme224 Properties
  • Lake Elsinore219 Properties
  • West Covina213 Properties
  • Woodland211 Properties
  • Cazadero208 Properties
  • Hemet201 Properties
  • Fremont200 Properties
  • Half Moon Bay200 Properties
  • San Anselmo194 Properties
  • Monrovia193 Properties
  • Santa Clarita187 Properties
  • McKinleyville179 Properties
  • Agoura Hills179 Properties
  • Rohnert Park178 Properties
  • Lakeshore175 Properties
  • San Bernardino175 Properties
  • Ridgecrest173 Properties
  • Kelseyville167 Properties
  • Kernville165 Properties
  • Torrance164 Properties
  • Albany163 Properties
  • Westlake Village154 Properties
  • Wrightwood143 Properties
  • Lakeport139 Properties
  • Santa Ynez137 Properties
  • Los Olivos136 Properties
  • Westwood126 Properties
  • Blairsden-Graeagle124 Properties
  • Big Sur123 Properties
  • Santee118 Properties
  • Playa Del Rey116 Properties
  • El Centro114 Properties
  • Squaw Valley113 Properties
  • San Gabriel110 Properties
  • Van Nuys99 Properties
  • Gardena95 Properties
  • San Simeon92 Properties
  • Homewood89 Properties
  • Needles81 Properties
  • Emeryville64 Properties
  • Moorpark55 Properties
  • Angelus Oaks46 Properties
  • Shasta Lake41 Properties
  • Long Barn32 Properties
  • La Jolla21 Properties
  • Warner Springs20 Properties