Holiday Rentals in Healdsburg

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Check prices for these dates

In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec

Holiday Rentals in Healdsburg

Our top choices for Healdsburg holiday rentals

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Fridge, microwave, oven, stovetop

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
View from property

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (320)
"The cabin was very clean and it was in a nice and quiet location."
The price is €150
includes taxes & fees
22 Sept - 23 Sept
Clear Lake Cottages & Marina
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
Smart TV, fireplace, DVD player, books

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

10.0 out of 10, Exceptional, (395)
"Absolutely amazing definitely plan on going back"
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!
7 Bedroom Oceanfront in Dillon Beach with spa
Dining

7 Bedroom Oceanfront in Dillon Beach with spa

9.4 out of 10, Exceptional, (162)
"We have a group of four families that stay here once a year. It's always a pleasure, and every time we stay we see a few more things are improved from the last time we were there... which is always nice to see."
The price is €1,557
includes taxes & fees
21 Sept - 22 Sept
7 Bedroom Oceanfront in Dillon Beach with spa
The Ranch at Lake Sonoma
Front of property

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 €57
includes taxes & fees
20 Sept - 21 Sept
The Ranch at Lake Sonoma
As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (89)
"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
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!
Interior

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

9.4 out of 10, Exceptional, (345)
"great location, ever better view for a lazy weekend"
The price is €579
includes taxes & fees
17 Oct - 18 Oct
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!
Riverfront Cottage in Wine Country - Seasonal River Access - Dogs Stay for Free!
Terrace/patio

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

9.8 out of 10, Exceptional, (342)
"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!
Oceanfront - Hot Tub - Newly Remodeled Cottage
Outdoor spa tub

Oceanfront - Hot Tub - Newly Remodeled Cottage

9.8 out of 10, Exceptional, (393)
"This property is in a great location located on the ocean in bodega Bay. Great ocean views, gardens, very clean property 12 minutes from restaurants hiking trails everywhere. We had a wonderful stay."
Oceanfront - Hot Tub - Newly Remodeled Cottage
Backyard Garden Oasis
Property grounds

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (50)
"Cute garden area, quiet, nice all inclusive spot"
The price is €183
includes taxes & fees
30 Sept - 1 Oct
Backyard Garden Oasis
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Interior

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (455)
"It was great as always"
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
Charming Bayfront Cottage with Gorgeous Views - Ideal for Quick Romantic Getaway
Beach nearby

Charming Bayfront Cottage with Gorgeous Views - Ideal for Quick Romantic Getaway

9.0 out of 10, Wonderful, (94)
"Beautiful view, litterally on tge water."
Charming Bayfront Cottage with Gorgeous Views - Ideal for Quick Romantic Getaway
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'
TV, fireplace, video games, DVD player

4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'

9.2 out of 10, Wonderful, (185)
"Property was adequate for our group of seven plus dog. Property is pet friendly. Excellent location. Good value."
4.5 Bedrooms, 3 Baths, 2 Kitchens, 180 degree views and a 'Man Cave'
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
Property grounds

Wildwood Gardens Scenic Rustic Vacation Retreat on the River

9.6 out of 10, Exceptional, (191)
"My husband and I enjoyed our stay in this home on the river. The decks, and large, private, river front yard were beautiful. "
Wildwood Gardens Scenic Rustic Vacation Retreat on the River
Luxury, Full Views, 6 Bedrooms/5 Full Baths, 3,800+ s.f., Pool Table, Hot Tub
Outdoor spa tub

Luxury, Full Views, 6 Bedrooms/5 Full Baths, 3,800+ s.f., Pool Table, Hot Tub

10.0 out of 10, Exceptional, (284)
"The house is absolutely gorgeous! We enjoyed the breathtaking sunset view just from the dinner table with wine at our hands. During the day, we can look out to the bay from every room. The house itself is spacious and comfortable, with the kitchen being the perfect gathering spot for the whole group. All the kitchen wares are provided for our convenience. The bathrooms are clean and comfortable. We had a great long weekend in the house and will definitely come back again next year!"
Luxury, Full Views, 6 Bedrooms/5 Full Baths, 3,800+ s.f., Pool Table, Hot Tub
Panoramic Ocean View--3 Min Walk To Beach
Dining

Panoramic Ocean View--3 Min Walk To Beach

9.6 out of 10, Exceptional, (321)
"We had a lovely stay in this cozy house with impeccable views of Dillon Beach. We had an amazing sunset one evening and it's just within a short walking distance right down to the water. "
Panoramic Ocean View--3 Min Walk To Beach
Gorgeously styled bungalow overlooking Bodega Harbor, Sauna, walk to town, Dogs
Fridge, oven, stovetop, dishwasher

Gorgeously styled bungalow overlooking Bodega Harbor, Sauna, walk to town, Dogs

9.8 out of 10, Exceptional, (96)
"We loved our stay in this comfortable, bright and airy cottage. Fantastic view of Bodega Bay from the front windows, and a pretty little garden and patio in the back. Kitchen is well equipped and spacious, beds are comfy. WiFi is good. It felt like home here."
Gorgeously styled bungalow overlooking Bodega Harbor, Sauna, walk to town, Dogs
'Wabi Tei' Serenity with Panoramic Ocean View. Hot Tub, BBQ, XBOX, WiFi, Pets OK
On the beach

'Wabi Tei' Serenity with Panoramic Ocean View. Hot Tub, BBQ, XBOX, WiFi, Pets OK

9.6 out of 10, Exceptional, (151)
"We had a wonderful time!! Thank you so much for making Wani-Tei available!!"
'Wabi Tei' Serenity with Panoramic Ocean View. Hot Tub, BBQ, XBOX, WiFi, Pets OK
Casa Bella Estate in Wine Country w/ New Pool!
Outdoor dining

Casa Bella Estate in Wine Country w/ New Pool!

9.6 out of 10, Exceptional, (131)
"Cozy Location for a Corporate retreat!"
The price is €2,783
includes taxes & fees
20 Sept - 21 Sept
Casa Bella Estate in Wine Country w/ New Pool!
Beautiful Lake Front Home on 5 acres...multi family vacations
Exterior

Beautiful Lake Front Home on 5 acres...multi family vacations

9.4 out of 10, Exceptional, (31)
"We had a great time at the property. The house and layout are great, and plenty of beds for everyone to sleep comfortably. Would recommend to all!"
Beautiful Lake Front Home on 5 acres...multi family vacations
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

H2Hotel

H2Hotel

10/10 Excellent
"Location can't be beat! Very comfortable, clean and great restaurants all within walking distance. Fun shops too. Only "negative" was the in-room coffee. 3 decaf 1 regular and we asked for just regular but had to go out every morning to get coffee so we both could get our caffeine hit. Other than that, highly recommend."
Maria 4-night trip
Posted 4 days ago
H2Hotel

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, apart-hotels, 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 €57 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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg: This highly rated holiday home rental in Healdsburg is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Healdsburg?

Expedia has 140 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.