Healdsburg holiday rentals

We found 577 holiday rentals — enter your dates for availability
Discover a selection of 140 homes, 10 apartments and other holiday rentals in Healdsburg that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for spending time at your holiday home, including parking and a TV. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Healdsburg

Showing deals for:20 Nov - 27 Nov

Terrace/patio
Interior
Interior
Pool
Exceptional
(21 reviews)

Modern Retreat - Spectacular View Home Above Dry Creek Valley

Healdsburg

8% off
S$13,303
for 7 nights, 1 home
S$1,900 per night
includes taxes & fees
Modern Retreat - Spectacular View Home Above Dry Creek Valley
Paths on the property
Large ranch-style home, 40-foot pool with full sun
Seat 14 for dining by the pool!
Dining expands to seat 12
Exceptional
(165 reviews)

Luxurious Large Home, Beautiful Pool, Extensive Gardens

Guerneville

12% off
S$11,848
for 7 nights, 1 home
S$1,693 per night
includes taxes & fees
Luxurious Large Home, Beautiful Pool, Extensive Gardens
Sprawling outdoor retreat with mountain views and ample parking
Main house
Bunkhouse studio unit
Main house
Exceptional
(40 reviews)

Sanctuary Estate - Wine Tastings Included

Healdsburg

8% off
S$27,370
for 7 nights, 1 home
S$3,910 per night
includes taxes & fees
Sanctuary Estate - Wine Tastings Included
Family room with sitting area, Smart TV and view of river
Riverside pool and deck with sitting area!
Large deck with two outdoor dining areas
Beautiful oak trees line the river bank
Exceptional
(36 reviews)

Perfect getaway! Riverside pool, river access, 5 min from Healdsburg square!

Healdsburg

8% off
S$5,780
for 7 nights, 1 apartment
S$826 per night
includes taxes & fees
Perfect getaway! Riverside pool, river access, 5 min from Healdsburg square!
Cottage path to gate.
Cottage from fire pit
Front of cottage in fall.
Living Room with Queen Size Sofabed
Exceptional
(241 reviews)

Healdsburg Cottage Walk to the Plaza, Workspace

Healdsburg

8% off
S$3,835
for 7 nights, 1 cottage
S$548 per night
includes taxes & fees
Healdsburg Cottage Walk to the Plaza, Workspace
Get cooking in style! Check out our chef's kitchen and cozy kitchen seating area.
Sit, Sip, and Savor with Vineyard Views - Perfect Outdoor Seating!
Centrally located with designer features and a view lounge over the vineyards, you will have a very memorable stay in wine country!
Unwind and reconnect with loved ones in the comfort of our inviting indoor space.
Exceptional
(6 reviews)

Vineyard View: Spa | Fire-pit | Dog Friendly

Sebastopol

8% off
S$10,641
for 7 nights, 1 home
S$1,520 per night
includes taxes & fees
Vineyard View: Spa | Fire-pit | Dog Friendly
Master bedroom
Patio area with grill and table
Gas range and large microwave oven
Front of the Guest House
Exceptional
(166 reviews)

Sapphire Canyon Vineyard Guest House

Geyserville

8% off
S$2,997
for 7 nights, 1 home
S$428 per night
includes taxes & fees
Sapphire Canyon Vineyard Guest House
Feast and relax in one place - our dining table just steps away living area!
TV time just got better! Catch your favorite shows on our big screen.
Elevate your dining experience with our charming outdoor seating!
Sleep like royalty in our king bed - your peaceful haven.
Exceptional
(10 reviews)

Tariff Discount: Romantic Retreat w/ Spa

Forestville

7% off
S$4,206
for 7 nights, 1 home
S$601 per night
includes taxes & fees
Tariff Discount: Romantic Retreat w/ Spa
Early Evening on the Plaza
Living Room
Living room
Vineyard Estate
Exceptional
(34 reviews)

Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

Cazadero

8% off
S$9,255
for 7 nights, 1 home
S$1,322 per night
includes taxes & fees
Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Arty Healdsburg will entice you

The area's wineries and art galleries are just some of the reasons to come on holiday to Healdsburg. Well known for its restaurants, riverfront and shopping, this walkable city won't disappoint. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Healdsburg

Are you hoping to find attractions to visit during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Healdsburg a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Jordan Vineyard & Winery (3.4 mi / 5.5 km)
  • Dry Creek Vineyard (4.2 mi / 6.8 km)
  • Francis Ford Coppola Winery (4.9 mi / 7.9 km)
  • Korbel Winery (8.8 mi / 14.1 km)
  • Kendall-Jackson Wine Estate and Gardens (9.1 mi / 14.6 km)
  • Russian River Vineyard (10.1 mi / 16.2 km)

Exploring the natural landscape of Healdsburg

Whether you're looking for adventure or just want to take in the scenery, Healdsburg is a great place to spend some time outside. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Russian River (4.4 mi / 7 km)
  • Armstrong Redwoods State Park (9 mi / 14.5 km)
  • Kendall-Jackson Wine Estate and Gardens (9.1 mi / 14.6 km)
  • Safari West (10.1 mi / 16.3 km)
  • Johnson's Beach (10.3 mi / 16.6 km)
  • Lake Sonoma (10.9 mi / 17.6 km)

Travelling to and around Healdsburg

The nearest airport is in Santa Rosa, CA (STS-Sonoma County), located 7.7 mi (12.5 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Healdsburg?
The most popular types of holiday rentals in Healdsburg are houses. Looking for something different? Vrbo has numerous options to match our guests' diverse needs, so you'll see holiday properties in all shapes and sizes, and for all budgets. The ideal home away from home is waiting for you — lock in yours today.
How much does it cost to rent a holiday rental in Healdsburg?
The average price for a holiday rental in Healdsburg is determined by a number of factors, including length of stay, season and property type. Whether you're in search of a sprawling villa with a pool or a comfy cabin that's perfect for two, just add your travel dates to find stays that offer great value.
How much does it cost to rent a beach house in Healdsburg?
Prices for beach houses in Healdsburg can vary depending on the style and size of the property and time of year you're travelling. All you have to do is enter your travel dates into Vrbo and how many guests to view holiday rental options and prices. From there you can use our filters to narrow down your search by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday rentals in Healdsburg?
Yes. There are. Choose from 15 holiday rentals that welcome pets in Healdsburg on Vrbo. Our furry friends deserve a getaway too, so simply use our search function for pet-friendly holiday rentals to find a property where your puppy dog can get in on the fun.
Can I rent a house with a pool in Healdsburg?
Pack your swimming gear and pool noodle, because there are three houses with a private pool in Healdsburg. Make a booking at one of these superb holiday homes and you'll enjoy pool days every day. Simply enter your dates into Vrbo, then check the "pool" filter to find the perfect place to make a splash!
What are popular rental amenities in Healdsburg?
Some of the most popular rental amenities people prefer in Healdsburg include mountain views, a chef and nearby museums. Whether you're holidaying with buddies, family or even pets, Vrbo holiday properties provide the best amenities for fun and relaxation with the people you love.
Are there large group holiday rentals in Healdsburg?
Take your pick of five Vrbo properties in Healdsburg that can host five or more guests. You'll get all the privacy and room you need to kick back with your loved ones — and nobody else.
Are there holiday rentals in Healdsburg that welcome kids?
Healdsburg has 15 family-friendly holiday rentals to pick from. And tracking down a stay that welcomes youngsters is super easy with Vrbo's "Properties good for families" filter. In addition to having the entire place to yourselves, you'll get perks and amenities such as dining rooms, yards and private pools.
What are the top attractions for families in Healdsburg?
Keeping the kids occupied during your holiday in Healdsburg is child's play with these top family-friendly attractions:
  • Pacific Coast Air Museum
  • Healdsburg Museum
  • Armstrong Redwoods State Park
Are there one-bedroom holiday rentals in Healdsburg?
Healdsburg has five one-bedroom rentals on offer. Often located in sought-after areas thanks to their smaller size, a one-bedroom holiday property is great if you're getting away with a pal or your partner. And with home comforts like full kitchens and more privacy than a standard hotel, you'll be able to relax while sightseeing around this incredible destination.
Can I find two-bedroom holiday rentals in Healdsburg?
Gather your loved ones and relax in total privacy and comfort in one of the five two-bedroom holiday rentals Healdsburg has to offer.
Are there holiday rentals with WiFi in Healdsburg?
Take your pick of seven holiday rentals with WiFi in Healdsburg. If you'd like to disconnect from the world during your escape, but still want to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Healdsburg?
Healdsburg has 15 holiday rentals where you can relax and recharge in air-conditioned comfort. To find a property on Vrbo that comes with this amenity, enter your travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Healdsburg?
The age limit can differ across properties on Vrbo, so double-check the rules of the holiday home in Healdsburg you're interested in. But typically, it's 16, 18 or 21.
How long can I rent a holiday rental in Healdsburg for?
How long you can book a holiday rental in Healdsburg differs according to the property. Just enter your chosen travel dates to look at a list of options offering extended stays. With plenty of amenities such as air conditioning and kitchens, as well as some offering weekly or monthly discounted prices, you're sure to find someplace just right to call your home away from home in Healdsburg.

More holiday ideas