Healdsburg Holiday Rentals

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Holiday Rentals in Healdsburg

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
Property grounds
Newly Refurbished! Nest Cottage at ru's Farm.
10.0 out of 10, Exceptional, (147)
"We went to Healdsburg to visit friends and enjoy the sunny weather. We were delighted with the beautiful vineyard views and comfortable cottage, spacious deck, and many other amenities that the host provided. Being in nature was so relaxing that we spent most of our time at the cottage."
Newly Refurbished! Nest Cottage at ru's Farm.
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
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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
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
Property grounds
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!
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
Wooded Restful Retreat, with broad scenic views, outdoor dining
10.0 out of 10, Exceptional, (276)
"The house is in a wooded residential area very close to downtown Healdsburg. The house was clean, modern and our host gave us many suggestions on restaurants and wineries."
Wooded Restful Retreat, with broad scenic views, outdoor dining
Outdoor pool
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
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
✨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 ✨
Interior
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
9.8 out of 10, Exceptional, (30)
"Super charming, very comfortable home - just a short stroll away from the main square. Made a great base for our family visit."
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
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
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
Outdoor pool, a heated pool
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
10.0 out of 10, Exceptional, (17)
"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
Property grounds
Bella Fattoria-HBG Farm to Table Hideaway
10.0 out of 10, Exceptional, (16)
"Family birthday celebration for the octogenarian patriarch. Property was just what we expected! Close to town to pop in for cocktails and dinner and far enough away to relax from the hustle and bustle. Clean, inviting, plenty of room inside and outside. We can’t wait to return for another trip!"
Bella Fattoria-HBG Farm to Table Hideaway
Fridge, microwave, oven, stovetop
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
Exterior
Rivers Breeze- Cabin only 10 min from Plaza!
10.0 out of 10, Exceptional, (4)
"Great place to stay!"
Rivers Breeze- Cabin only 10 min from Plaza!
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 HK$851
per night
16 May - 17 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
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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, (1004)
"Room was comfortable and staff was grand."
The price is HK$1,168
per night
21 May - 22 May
Best Western Dry Creek Inn
Front of property – evening/night
Hotel Trio Healdsburg
3.0 star property
9.4 out of 10, Exceptional, (644)
"Good quality for a fair price. "
The price is HK$1,539
per night
21 May - 22 May
Hotel Trio Healdsburg
Courtyard
The Lodge at Healdsburg, Tapestry Collection by Hilton
3.5 star property
8.8 out of 10, Excellent, (126)
"Very comfortable bed with soaking tub and fireplace in room. Pool and jacuzzi etc very clean and the courtyard with beautiful garden. Will stay there again. "
The price is HK$1,286
per night
4 Jun - 5 Jun
The Lodge at Healdsburg, Tapestry Collection by Hilton
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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Look no further and take a look at our great range of rental properties in Healdsburg!

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

Hotel Trio Healdsburg

Hotel Trio Healdsburg

5/5 Excellent
"Good quality for a fair price. "
A verified traveller from chandler stayed at Hotel Trio Healdsburg
Posted 4 days ago
Hotel Trio Healdsburg