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Healdsburg Vacation Rentals

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  2. United States of America
  3. California
  4. Healdsburg

Our Favorite Vacation Rentals in Healdsburg

  • 3BR w/ Pool, Hot Tub & Guest Suite
     3br Home/Apartment
    RedAwning
    From
    $1,480
  • Downtown Suites One
     Home/Apartment
    Booking.com
    From
    $263
  • Serene Riverfront Cottage ­ In Healdsburg, Views, Kayaks, 1.5 Mile to Downtown
     2br Home/Apartment
    HolidayLettings
    From
    $406
  • 4BR Rocktop Lodge w/ Pool & Hot Tub
     4br Home/Apartment
    RedAwning
    From
    $1,428
  • The Eastside - Healdsburg Family Farmhouse Home
     Country House
    Booking.com
    From
    $726
  • Dreamy Wine Country Family Estate
     4br Home/Apartment
    HolidayLettings
    From
    $2,147
  • Quiet Wine Country Home w/ Private Pool & Hot Tub
     4br Home/Apartment
    RedAwning
    From
    $1,156
  • Adventure on the River
     Glamping
    Booking.com
    From
    $125
Show all

Check prices for these upcoming dates

Healdsburg Vacation Rentals with a Pool

  • 3BR on 7 Acres w/ Hot Tub & Pool
     3br Home/Apartment
    RedAwning
    From
    $700
  • Family Friendly WineCountry Retreat
    Excellent4br Home/Apartment
    Airbnb
    From
    $2,091
  • Xanadu Healdsburg
     4br Home/Apartment
    Airbnb
    From
    $1,266
  • Guest Suite Surrounded by Dry Creek Vineyards
    ExcellentHome/Apartment
    Airbnb
    From
    $333
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Healdsburg Vacation Rentals with Wi-Fi

  • Wine Country Retreat w/ Hot Tub, Deck & Fireplace
     3br Home/Apartment
    RedAwning
    From
    $694
  • Villa Tranquila
     5br Villa
    RedAwning
    From
    $1,394
  • Dry Creek Valley Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $195
  • Wine Country Cottage in Healdsburg
    ExcellentHome/Apartment
    Airbnb
    From
    $217
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Healdsburg Pet-Friendly Vacation Rentals

  • Stunning vineyard views from the private deck at this wine-lovers house!
     3br Home/Apartment
    HolidayLettings
    From
    $687
  • Yea, The Outdoor Kitchen IS a Little Crazy
     3br Home/Apartment
    HolidayLettings
    From
    $1,553
  • Dog-friendly home with a deck, patios, & hot tub - in the heart of wine country!
     2br Home/Apartment
    HolidayLettings
    From
    $382
  • Close to Healdsburg Plaza with Vineyard Views!
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $514
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.

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Price and Availability in Healdsburg

Most expensive
Most availability
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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.
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The Weather in Healdsburg

Rainy days
74° 30°
10
61° 30°
17
78° 29°
7
97° 45°
1
85° 40°
3
104° 47°
0
96° 48°
0
104° 51°
0
106° 38°
0
95° 32°
0
79° 28°
1
61° 31°
9
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Healdsburg. The warmest months in Healdsburg are April and July, when temperatures reach 106 ˚F. The coolest month is February, when temperatures drop to 28 ˚F. The wettest month in Healdsburg is November with 17.18 inches of rain, while the driest month is September with 0.98 inches of rain.

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What Expert Travelers Think

  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
    Visit Tammymum

  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
    KaelinKindly Kae
    Visit Kindly Kae

  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly
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Vacation Rentals in Healdsburg

Browse accommodations from all the leading providers including Airbnb, Priceline, RedAwning and more at AllTheRooms.com. AllTheRooms has 652 rentals, hotels and other great places to stay while you enjoy Healdsburg, with everything from inexpensive hostels and homestays to luxury Airbnbs and hotels. A vacation in Healdsburg can be budget-friendly - our cheapest price accommodation is available at $10 per night. An average rental in Healdsburg costs on average $589 a night.

If you need internet access during your time in Healdsburg, then you can choose from over 215 accommodations that have WiFi internet. 41 places to stay include a morning meal. You can maintain your workout routine by staying at one of 17 accommodations that provide gym facilities. Driving to Healdsburg? Then choose one of the 216 places to stay that comes with a parking spot included. 74 accommodations come with a pool or jacuzzi

AllTheRooms has 53 pet-friendly places to stay in Healdsburg, so if you're traveling with your cat or dog you won't have any problems.

We combine a wide variety of Healdsburg accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 4 providers, including 198 places to stay from Airbnb, 24 accommodations from Priceline and 5 places to stay from RedAwning.

373 accommodations in Healdsburg have been reviewed; 68% are rated excellent or good. 187 places to stay in are instantly bookable.

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