Compare Healdsburg Vacation Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Healdsburg Rentals

Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping

1 out of 5
2411 Alexander Valley Rd Healdsburg CA
3.83 mi from city center
$98 nightly
The price is $112 total per night
$112 total
Nov 23 - Nov 24
Total with taxes and fees
Guests staying at Wildhaven Sonoma Glamping enjoy a private beach, free WiFi in public areas, and a terrace. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Additional amenities include a convenience store, a water dispenser, and barbecue grills.
Kitchen
Pet friendly
Wine Country Retreat with Panoramic Views-5 min from downtown Healdsburg

Wine Country Retreat with Panoramic Views-5 min from downtown Healdsburg

Healdsburg CA
1 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a water dispenser.
Kitchen
Washer
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental

Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental

Healdsburg CA
0.44 mi from city center
At this vacation home, guests enjoy an outdoor pool, a gym, and a hot tub. Other amenities at this family-friendly vacation home include an arcade/game room, laundry facilities, and local meal delivery service.
Pool
Hot Tub
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Healdsburg CA
2.28 mi from city center
Guests staying at this vacation home enjoy an outdoor pool, a gym, and a hot tub. Other amenities at this family-friendly vacation home include laundry facilities, local meal delivery service, and a garden.
Pool
Hot Tub
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

Healdsburg CA
2.89 mi from city center
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Kitchen
Washer
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

Healdsburg CA
3.85 mi from city center
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Healdsburg CA
5.53 mi from city center
$1,727 nightly
The price is $1,912 total per night
$1,912 total
Oct 25 - Oct 26
Total with taxes and fees
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Transportation is made easy with limo/town car service. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this golf vacation home include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
Spacious house in marvelous Healdsburg close to town

Spacious house in marvelous Healdsburg close to town

Healdsburg CA
1.02 mi from city center
At this vacation home, guests have access to a garden.
Kitchen
Pet friendly
Secluded Vineyard Estate Healdsburg

Secluded Vineyard Estate Healdsburg

Healdsburg CA
2.74 mi from city center
This villa features a hot tub, a terrace, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Hot Tub
Sanctuary Estate - Wine Tastings Included

Sanctuary Estate - Wine Tastings Included

Geyserville CA
3.48 mi from city center
$4,147 nightly
The price is $4,628 total per night
$4,628 total
Oct 27 - Oct 28
Total with taxes and fees
Guests of this vacation home enjoy features like a gym, a hot tub, and laundry facilities. Other amenities at this family-friendly vacation home include a garden and barbecue grills.
Hot Tub
Kitchen
Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included

Healdsburg CA
0.55 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
6Beds 3Bath - Pool, Hot Tub, Pets Welcome, Fire Pit- 1mi to Downtown

6Beds 3Bath - Pool, Hot Tub, Pets Welcome, Fire Pit- 1mi to Downtown

Healdsburg CA
1.09 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and laundry facilities. Other amenities at this family-friendly vacation home include a garden and barbecue grills.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Healdsburg
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Healdsburg Large Group Rentals

How to Book Vacation Rentals in Healdsburg



🏠 What is the best price for Healdsburg vacation rentals?

Healdsburg vacation rentals range in price, starting at $112 per night.


🏠 What types of vacation rentals in Healdsburg can I rent?

Orbitz offers a wide range of Healdsburg rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Healdsburg condo rentals.


🏠 Is it free to cancel my Healdsburg vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Healdsburg vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Healdsburg. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Healdsburg?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Healdsburg apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Healdsburg?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Healdsburg package deals will get you even more savings.