Healdsburg Vacation Rentals

See all 730 deals in Healdsburg

Our Favorite Vacation Rentals in Healdsburg

  • Villa Tranquila
     5br Villa
    RedAwning
    From
    $1,440
  • Urban Luxe Loft
    ExcellentHome/Apartment
    Booking.com
    From
    $595
  • River View - Riverfront Getaway in Healdsburg - Hot tub, Kayaks, River Access
     3br Home/Apartment
    HolidayLettings
    From
    $613
  • Magnum in a Wine Glass
     Villa
    Booking.com
    From
    $1,800
  • Stunning vineyard views from the private deck at this wine-lovers house!
     3br Home/Apartment
    HolidayLettings
    From
    $657
  • 788 Magnolia Dr Entire Property Home
     Country House
    Booking.com
    From
    $1,447
  • New Contemporary Wine County Home
     3br Home/Apartment
    HolidayLettings
    From
    $959
  • The Eastside - Healdsburg Family Farmhouse Home
     Country House
    Booking.com
    From
    $1,099

Check prices for these upcoming dates

Healdsburg Vacation Rentals with a Pool

  • Family Friendly WineCountry Retreat
    Excellent4br Home/Apartment
    Airbnb
    From
    $2,091
  • Guest Suite Surrounded by Dry Creek Vineyards
     Home/Apartment
    Airbnb
    From
    $333
  • Alexander Valley Lodge Pool/Hot Tub
    Excellent5br Home/Apartment
    Airbnb
    From
    $927
  • Dog Friendly Healdsburg / Dry Creek Valley Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $565

Healdsburg Vacation Rentals with Wi-Fi

  • The Woods Resort - A Gay Friendly Resort
    Nice19br 3-star Home/Apartment
    Booking.com
    From
    $149
  • Wine Country Cottage in Healdsburg
    ExcellentHome/Apartment
    Airbnb
    From
    $243
  • Paxton Guesthouse
    ExcellentHome/Apartment
    Airbnb
    From
    $283
  • Affordable Fitch Mountain Cabin
    Excellent2br Cabin
    Airbnb
    From
    $412

Healdsburg Pet-Friendly Vacation Rentals

  • Dog-friendly home with a deck, patios, & hot tub - in the heart of wine country!
     2br Home/Apartment
    HolidayLettings
    From
    $446
  • Close to Healdsburg Plaza with Vineyard Views!
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $514
  • Wine Sippin Escape
     Home/Apartment
    HolidayLettings
    From
    $219
  • Dog-friendly cabin beneath towering redwoods w/ an enclosed yard - near river
     2br Home/Apartment
    HolidayLettings
    From
    $267

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
98 º44
0
91 º44
1
91 º32
5
69 º35
3
74 º37
6
84 º27
0
91 º33
6
86 º36
3
93 º44
0
103 º45
0
74 º37
6
103 º50
0
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Healdsburg. The warmest months in Healdsburg are July and May, when temperatures reach 103 ˚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

  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide
  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen

Vacation Rentals in Healdsburg

Browse vacation rentals from all the leading providers including Airbnb, RedAwning, Priceline and many more at AllTheRooms.com. We have 727 vacation rentals, hotels and other places to stay in Healdsburg ranging from low-cost options to extravagant places to stay. If you are wanting to save money, the cheapest place to stay in Healdsburg is just $32 a night. The average price of an accommodation is $617 per night.

If you need an internet connection during your stay in Healdsburg, then you can choose from over 286 places to stay that provide WiFi internet. 41 of our accommodations come with breakfast in the price. Fitness addicts can get a workout in during their stay by choosing from 23 accommodations that have gyms. If you are driving to Healdsburg, you'll want to pick from 285 places to stay that provide parking. 72 places to stay come with a pool or jacuzzi

Those traveling with a cat, dog or some other animal can stay in any of 79 accommodations that are designated as pet-friendly.

In Healdsburg AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 5 providers, including 188 places to stay from Airbnb, 5 accommodations from RedAwning and 5 places to stay from Priceline.

400 accommodations in Healdsburg have been reviewed; 69% are rated excellent or good. 172 accommodations allow instant booking.

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