Healdsburg Holiday Rentals

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Holiday Rentals in Healdsburg

Chalk Hill Cottage Close to Wineries
10.0 out of 10, Exceptional, (11)
"We really enjoyed our stay at the Chalk Hill Cottage. It was clean and well set up. The bed was extremely comfortable. It was rainy and wet all weekend so we are hoping to book this cottage again so we can enjoy the outdoor area including the gas firepit."
Chalk Hill Cottage Close to Wineries
Bella Fattoria-HBG Farm to Table Hideaway
10.0 out of 10, Exceptional, (14)
"The property was exactly as what we expected! It was a quiet, relaxing stay in the countryside. The house was clean and the check-in process was straightforward. We will be looking at returning to this place again in the future."
Bella Fattoria-HBG Farm to Table Hideaway
Newly Refurbished! Nest Cottage at ru's Farm.
10.0 out of 10, Exceptional, (146)
"Lovely cottage for our extended weekend stay. Beautiful facility, quiet, clean and 5 minutes from downtown Healdsburg. We will stay here again if we come back! The bathroom and shower is small ( we didn’t mind but it is tight). Host was very kind and communication about check-in/ check-out was super easy!"
Newly Refurbished! Nest Cottage at ru's Farm.
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Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat
10.0 out of 10, Exceptional, (14)
"For a girls weekend, we stayed at this gorgeous home in Healdsburg. We were greeted by Adam who'd kindly set up a private wine tasting next door, where we enjoyed a wonderful history of the property, while tasting delicious wines... (and purchasing quite a few:) The home itself was bright, an open layout and comfortably housed five ladies. Every detail was impressive, from the gas fireplace, yoga mats, and even earplugs, just in case. Location was close to town, easy freeway access (without the...
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat
Private Vineyard Haven--walk to the HBG Square!
9.8 out of 10, Exceptional, (38)
"Fantastic location! Super clean, easy check in process. Had Evette needed and the house just truly completed and enhanced our visit to wine country!"
Private Vineyard Haven--walk to the HBG Square!
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
10.0 out of 10, Exceptional, (147)
"Wonderful property, perfect for a get away. All amenities are top notch! Thank you!"
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Healdsburg Cottage Walk to the Plaza, Workspace
10.0 out of 10, Exceptional, (201)
"We had an wonderful stay in this Magical Gardens Cottage nestled in a myriad of foliage & flowers. Bees were buzzing and the flowers were calming and downright magical. Paco, our new dog friend welcomed us into his domain (we loved Paco). Our hosts were attentive and welcoming. The cottage is just a shot walk into Healdsburg Square and in close proximity to a myriad of wineries for some very tasty tastings. The cottage was clean & comfortable, we had a lovely stay!"
Healdsburg Cottage Walk to the Plaza, Workspace
Dry Creek Cottage - Healdsburg
9.8 out of 10, Exceptional, (131)
"Second time at this property- it’s quiet and relaxing. The pool and hot tub felt amazing after a long day of exploring."
Dry Creek Cottage - Healdsburg
B - Wine Country Getaway
9.6 out of 10, Exceptional, (7)
"Really nice unit with good furniture and really nice amenities. one of the things that was nice was it felt very private in a secluded part of the valley, but was easily accessible to get to nearby Healdsburg and lots of wineries."
B - Wine Country Getaway
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!
10.0 out of 10, Exceptional, (19)
"We had a great time. Beautiful property. Picky but why not buy a new iron and ironing board for each house. We had to carry one iron from house to house. You Could spend $100 and be done. I felt like our group went above and beyond to clean and take care of the place while we were there."
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣‍♀️ Semi-Private Beach🏖Lux Spa
9.6 out of 10, Exceptional, (155)
"We will be staying here again! Love Healsburg, love the wine, and this house was a great way to enjoy it. Stephen and Tay were wonderful hosts and they sincerely work to make your stay enjoyable. The house, elevated on the hillside, has amazing views, is clean and has everything you need for a great vacation in wine country. Highly recommend."
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣‍♀️ Semi-Private Beach🏖Lux Spa
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country
9.8 out of 10, Exceptional, (17)
"Loved Staying at this special place. We had family travel to Healdsburg for a wedding. They did not want to leave the house."
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country
Dog-friendly home on 10 acres w/private hot tub, English garden, patio
10.0 out of 10, Exceptional, (28)
"The house was perfect for our family Thanksgiving stay. The kitchen was well equipped and very organized. The property is beautiful with a lovely vista overlooking the leaf changing vineyard. The main road was a bit busy and not conducive to walks but noise was not too bad. The management company was very communicative. Would recommend to others."
Dog-friendly home on 10 acres w/private hot tub, English garden, patio
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
10.0 out of 10, Exceptional, (45)
"Beautiful property on a nice location just to the east of the 101. 5-10 minute ride to downtown healdsburg and plenty of open space to bbq, play lawn games or lounge by the beautiful pool. my friends and i love to cook so the kitchen was well appointed and the pantry decently stocked. Highly recommend for big groups"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Hidden Oasis ~ a Private Luxury Home in Healdsburg
10.0 out of 10, Exceptional, (9)
"This home is so perfect for 4 couples to share. Fabulous stocked kitchen and beautiful family room and outdoor entertainment space. New, clean, up to date and luxury at its best. This is the second time we have stayed here and will probably use it again next fall. It’s becoming our home away from home."
Hidden Oasis ~ a Private Luxury Home in Healdsburg
Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining
Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining
Close to Plaza/15 Acre Estate/Swimming Pool and Bocce Ball
9.8 out of 10, Exceptional, (110)
"We really enjoyed Don’s place for a getaway with friends and our small children. The living room and outdoor space were great for groups"
Close to Plaza/15 Acre Estate/Swimming Pool and Bocce Ball
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
10.0 out of 10, Exceptional, (16)
"Great convenient location right in center of Healdsburg. Leah, our host, was attentive and knowledgable, and went out of her way to make sure our stay was going well. Would come back!"
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
Wooded Restful Retreat, with broad scenic views, outdoor dining
10.0 out of 10, Exceptional, (275)
"The property was well appointed and supplied, and the view from the deck is breathtaking! We were very comfortable, and recommend this retreat on Fitch mountainside!"
Wooded Restful Retreat, with broad scenic views, outdoor dining
Healdsburg Home with Magnificent Vineyard View by RedAwning
10.0 out of 10, Exceptional, (16)
"House is as advertised. Property manager was prompt and helpful. We will be back!"
Healdsburg Home with Magnificent Vineyard View by RedAwning
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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 Holiday Home Travel Info

Other types of properties in Healdsburg you may be interested in

Best Western Dry Creek Inn
3.0 star property
7.8 out of 10, Good, (1005)
"Would be great if they had plugs for chargers by the bed. Had to move bed away from wall, unplug lights to be able to plug in phone. Otherwise a quick and uneventful stay for a reasonable price. Looking forward to the restaurant in the parking lot to open again."
The price is AU$264
includes taxes & fees
5 May - 6 May
Best Western Dry Creek Inn
Hotel Trio Healdsburg
3.0 star property
9.4 out of 10, Exceptional, (638)
"We was really pleased with our stay "
The price is AU$376
includes taxes & fees
7 May - 8 May
Hotel Trio Healdsburg
Harmon Guest House
3.0 star property
9.4 out of 10, Exceptional, (316)
"Perfect except for the significant street noise! "
The price is AU$758
includes taxes & fees
5 May - 6 May
Harmon Guest House
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.

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 favourite 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 depend 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 per night. Entering your travel dates in the search wizard might find you 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?

COZY Bungalow--Dog-Friendly—Perfect for Couples!!! : This holiday home rental outside of Healdsburg is located on the waterfront, and offers a selection of books, a Smart TV and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Healdsburg?

Expedia has 142 holiday rentals for your stay in Healdsburg.

What can I see and do in Healdsburg?

Enjoy the outdoors at Russian River and Austin Creek State Recreation Area, or simply take in cultural attractions like Healdsburg Museum and Raven Performing Arts Theater. Healdsburg Plaza and Mazzocco 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.

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