Holiday Rentals in Healdsburg

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Holiday Rentals in Healdsburg

Property grounds
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
10.0 out of 10, Exceptional, (148)
"Wonderful property, perfect for a get away. All amenities are top notch! Thank you!"
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Golf
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣‍♀️ Semi-Private Beach🏖Lux Spa
9.6 out of 10, Exceptional, (156)
"We had a great experience at Fitch Mountain Lookout. The home has a great view, is a short walk downhill to the river, and only a short drive to town. We most enjoyed watching the birds come to the feeders in the morning while we started our day in the hot tub!"
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣‍♀️ Semi-Private Beach🏖Lux Spa
Exterior
Chalk Hill Cottage Close to Wineries
10.0 out of 10, Exceptional, (12)
"We recently stayed at Chalk Hill Cottage with our two little Yorkies. The property was the perfect size and had first class amenities. The location is awesome, too! The Hosts are quick to respond to questions and are very kind and considerate. We recommend highly!"
Chalk Hill Cottage Close to Wineries
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Fridge, microwave, oven, stovetop
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
A heated pool
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!
Property grounds
Newly Refurbished! Nest Cottage at ru's Farm.
10.0 out of 10, Exceptional, (148)
"We thoroughly loved staying here!!!"
Newly Refurbished! Nest Cottage at ru's Farm.
A heated pool
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!
10.0 out of 10, Exceptional, (20)
"Amazing house. Very expensive but worth it if you have a big group and want a nice pool. High end kitchen and comfortable large beds in every room. We had one moderate issue where the fire pit was broken and the host responded quickly and replaced it the next day, good communication. Would rent here again."
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!
Pool
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views
10.0 out of 10, Exceptional, (133)
"Beautiful central location, comfortable and clean. Just slightly dated."
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views
Fridge, microwave, oven, stovetop
Wooded Restful Retreat, with broad scenic views, outdoor dining
10.0 out of 10, Exceptional, (278)
"We were so impressed the first time that we stayed here, we had to come back again. The house is beautiful and perfect for two couples. And the view from the deck...amazing!"
Wooded Restful Retreat, with broad scenic views, outdoor dining
Fridge, microwave, oven, stovetop
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
10.0 out of 10, Exceptional, (262)
"Very well appointed, well equipped restored cabin with bucolic views of acres of vineyards. It is located in a one lane road that could frighten some off. It’s a short ride into Healdsburg and surrounding attractions. The owners are friendly and hands on and responded to every need promptly. We loved this spot and would do it all over again."
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
Property grounds
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country
9.8 out of 10, Exceptional, (19)
"We loved this property! We did a mini high school reunion with friends from 40 years ago. The house was amazing and did not disappoint at all. We laid by the pool, played cards outside. Close to Healdsburg Square (7 minutes away). This trip was beyond all our expectations and the house was clean and big and the view was amazing. Recommend for a group of 8 or less. We will definitely book again!"
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country
Property grounds
Bella Fattoria-HBG Farm to Table Hideaway
10.0 out of 10, Exceptional, (18)
"**Review for Our VRBO Stay: A Perfect Getaway** We recently had the pleasure of staying at the stunning Bella Fattoria property and couldn't be more thrilled with our experience. From the moment we arrived, it was clear that this home was something special. The beautiful decorations throughout the house immediately caught our eye, creating a warm and inviting atmosphere that made us feel right at home. Every detail seemed to be thoughtfully considered, and the property truly checked off all...
Bella Fattoria-HBG Farm to Table Hideaway
Property grounds
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
Property grounds
Healdsburg Cottage Walk to the Plaza, Workspace
10.0 out of 10, Exceptional, (205)
"This cottage was by far one of best we have stayed in. Immaculate, charming, everything we needed. Lovely!"
Healdsburg Cottage Walk to the Plaza, Workspace
Pool
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
Fridge, microwave, oven, stovetop
B - Wine Country Getaway
9.6 out of 10, Exceptional, (8)
"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
Outdoor pool, a heated pool
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
10.0 out of 10, Exceptional, (17)
"We had a great time celebrating our daughter’s wedding. The house was the focal point of the weekend and was fantastic! Great place for a family celebration!"
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
Fridge, microwave, oven, stovetop
Beautiful Cottage overlooking vineyards. Three minutes from downtown!
10.0 out of 10, Exceptional, (213)
"Lovely property and convenient."
Beautiful Cottage overlooking vineyards. Three minutes from downtown!
Property grounds
E - Tiny Home, Big Feel - Just minutes from town and Sonoma County Airport!
8.8 out of 10, Excellent, (3)
"Really nice private area on the property - for the review about the wifi - it worked wonderful - was gone during the day but relaxing and good vibe when I was there. Nice outside area as well."
The price is €135
includes taxes & fees
23 May - 24 May
E - Tiny Home, Big Feel - Just minutes from town and Sonoma County Airport!
A heated pool
Healdsburg Modern Limerick, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi
10.0 out of 10, Exceptional, (7)
"The property was awesome exactly as depicted in the pictures house is completely updated with huge open living area/kitchen on first floor so everyone can hang out together and great outdoor lounging space with BBQ/pool/spa. Would definitely go back again."
Healdsburg Modern Limerick, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi
Don't see what you're looking for?
See all available properties in Healdsburg
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.

Other types of properties in Healdsburg you may be interested in

Outdoor pool, open 7:00 AM to 10:00 PM, pool loungers
Best Western Dry Creek Inn
3.0 star property
7.8 out of 10, Good, (1003)
"Clean, friendly staff, very convenient location"
The price is €160
includes taxes & fees
27 May - 28 May
Best Western Dry Creek Inn
Front of property – evening/night
Hotel Trio Healdsburg
3.0 star property
9.4 out of 10, Exceptional, (645)
"We loved our stay in this hotel. Everything from the room ( all the rooms are suite style) to the property was excellent. Good options for breakfast (included) and shuttle downtown was very convenient. Staff at the reception was very friendly and helpful. We would be definitely coming back "
The price is €228
includes taxes & fees
28 May - 29 May
Hotel Trio Healdsburg
Room, 2 Queen Beds, Non Smoking
Fairview Inn and Suites
2.0 star property
7.4 out of 10, Good, (885)
"The room was clean. Temperature was perfect. Great proximity to the Town without paying "town prices". I couldn't check in until 4pm, but the office allowed me to store my bags there until I checked in. "
The price is €128
includes taxes & fees
23 May - 24 May
Fairview Inn and Suites
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, 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 €135 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?

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.

Recent reviews of Healdsburg properties
Expedia verified reviews

Fairview Inn and Suites

Fairview Inn and Suites

5/5 Excellent
Great deal for the area!
"The room was clean. Temperature was perfect. Great proximity to the Town without paying "town prices". I couldn't check in until 4pm, but the office allowed me to store my bags there until I checked in. "
A verified traveller stayed at Fairview Inn and Suites
Posted 2 days ago
Fairview Inn and Suites