Healdsburg Holiday Rentals

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Holiday Rentals in Healdsburg

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

10.0 out of 10, Exceptional, (63)
"Gorgeous property and excellent communications with owner and property manager. Well stocked kitchen and so many wonderful things to enjoy!"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (320)
"Great stay!"
The price is NZ$288
includes taxes & fees
26 Oct - 27 Oct
Clear Lake Cottages & Marina

As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley

9.8 out of 10, Exceptional, (91)
"The house was phenomenal and we truly enjoyed our stay. The bedrooms all have large beds and bathrooms and are separate which provided nice privacy. The hot tub, common areas, and view were all amazing."
As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley

Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

10.0 out of 10, Exceptional, (397)
"We love this rental! Perfect for a couple or a family that doesn’t mind sharing a bed :) amazing hosts and most incredible view. "
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

The Ranch at Lake Sonoma

1.0 star property
10.0 out of 10, Exceptional, (1)
"The location is fantastic, with a spectacular view on the lake if you choose a lakeview. A very genuine welcome from The Ranch team, with all detailed explanations, a map to help you to navigate around. For our first time going camping, we want definitely to come back there !"
The price is NZ$117
includes taxes & fees
4 Oct - 5 Oct
The Ranch at Lake Sonoma

7 Bedroom Oceanfront in Dillon Beach with spa

9.4 out of 10, Exceptional, (162)
"Amazing property with stunning views. Owner is prompt with communication, and the amenities are as advertised. Would stay again or recommend to anyone!"
The price is NZ$3,481
includes taxes & fees
1 Oct - 2 Oct
7 Bedroom Oceanfront in Dillon Beach with spa

COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!

9.6 out of 10, Exceptional, (186)
"Perfect get away for my wifes 60th."
COZY—Dog-Friendly—Perfect for Couples!!! 2025 DISCOUNT for 5-10 days—ASK!!!

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (393)
"Perfect getaway and the hot tub was a hit. "
Oceanfront - Hot Tub - Newly Remodeled Cottage

Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

9.8 out of 10, Exceptional, (344)
"We enjoyed our stay at this well equipped and designed cottage. We loved the decks and location on the river. "
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (456)
"It was great as always"
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true

10.0 out of 10, Exceptional, (281)
"Lovely house, setting and host!"
Romantic, Dramatic Views! Full calendar https://www.vrbo.com/81742?dateless=true

Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

9.4 out of 10, Exceptional, (346)
"The property was beautiful and perfect! We absolutely loved our stay here, and are looking forward to coming back again."
The price is NZ$949
includes taxes & fees
1 Oct - 2 Oct
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

10.0 out of 10, Exceptional, (66)
"Smooth check-in process. Close to plenty of vineyards. Very friendly staff. "
Exquisite Wine Country Villa, Winery And Wine Cave, Villa Montebella

Panoramic Ocean View--3 Min Walk To Beach

9.6 out of 10, Exceptional, (322)
"The cabin is well supplied and so close to the beach. Comfortable and sweet."
Panoramic Ocean View--3 Min Walk To Beach

Sonoma Luxury, Enchanting Sonoma Home, Walkable to the Square, Sleeps 10

9.8 out of 10, Exceptional, (154)
"Beautiful property in a good location not far from Sonoma Square. Our friends really enjoyed staying there !"
Sonoma Luxury, Enchanting Sonoma Home, Walkable to the Square, Sleeps 10

Bright Home 800 Feet from Salmon Creek Beach w/ Wood Stove & Pool Table

8.2 out of 10, Very good, (47)
"Walking distance to the beach and a warm and inviting space to return to. Perfect for our weekend getaway."
Bright Home 800 Feet from Salmon Creek Beach w/ Wood Stove & Pool Table

Casa Bella Estate in Wine Country w/ New Pool!

9.6 out of 10, Exceptional, (132)
"Cozy Location for a Corporate retreat!"
Casa Bella Estate in Wine Country w/ New Pool!

Malibu of the North Oceanfront w 3 Suites

7.8 out of 10, Good, (8)
Malibu of the North Oceanfront w 3 Suites

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

10.0 out of 10, Exceptional, (245)
"Loved the house and location! "
The price is NZ$4,122
includes taxes & fees
1 Oct - 2 Oct
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Luxe Surf Shack | Rooftop Hot Tub, Games + Near Beach

10.0 out of 10, Exceptional, (21)
"The house was fantastic and in a great location. We'd definitely stay here again on future trips."
Luxe Surf Shack | Rooftop Hot Tub, Games + Near Beach
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.
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Top Healdsburg Hotel Reviews

Find out more about Healdsburg

Find out more about Healdsburg

Everything you need to know about Healdsburg holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Healdsburg holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Healdsburg holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Healdsburg holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Healdsburg. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Healdsburg holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Healdsburg holiday rentals we have selected for you start as low as NZ$117 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Healdsburg rentals

At Expedia, we put the best Healdsburg holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Healdsburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Healdsburg holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Healdsburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Healdsburg?

Yes, there are holiday rentals in Healdsburg close to SingleThread Farm at Dry Creek, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and scenic riverfront in Healdsburg. While you're here, grab a bite or have a drink at the wineries and top-notch restaurants.

What are some of the best holiday rentals that Healdsburg has to offer?

7 Bedroom Oceanfront in Dillon Beach with spa: This holiday home rental outside of Healdsburg is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Healdsburg?

Expedia has 139 holiday rentals for your stay in Healdsburg.

What can I see and do in Healdsburg?

Enjoy the outdoors at Russian River and Healdsburg Ridge Open Space Preserve, or simply take in cultural attractions like Healdsburg Museum and Raven Performing Arts Theater. Healdsburg Plaza and Jordan Vineyard & Winery are other places to visit while you're in town.

What are holiday rentals like in Healdsburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Healdsburg. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.