Healdsburg Vacation Rentals

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

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

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

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

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.

Price and Availability in Healdsburg

Most expensive
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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.

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.

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
  • — 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
  • — 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

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.

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