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.
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
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A heated pool
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!
Fridge, microwave, oven, stovetop
Wooded Restful Retreat, with broad scenic views, outdoor dining
10.0 out of 10, Exceptional, (276)
"We stayed four nights at this beautiful home with another couple. We were impressed with the comfort, peacefulness, adequate space, and the beauty of the look-out from the deck. We all agreed it could not have been a better location. Close to Healdsburg, but felt like we were in a treehouse retreat. The host went above and beyond to help me understand the pricing and fee structure of the reservation, was very responsive to an allergy issue, and had taken the time to put little notes around the...
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 ✨
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, (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
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
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!
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
Property grounds
Dog-friendly home on 10 acres w/private hot tub, English garden, patio
10.0 out of 10, Exceptional, (29)
"Great property with 10 mins from Healdsburg Plaza."
Dog-friendly home on 10 acres w/private hot tub, English garden, patio
Exterior
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
Outdoor dining
Lily Pad Ranch--5 minutes to the HBG Plaza
10.0 out of 10, Exceptional, (12)
"The property was secluded yet very accessible to many of the wineries located in Healdsburg. Would definitely recommend as a stay for anyone travelling to that area."
Lily Pad Ranch--5 minutes to the HBG Plaza
Fridge, microwave, oven, stovetop
Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.
10.0 out of 10, Exceptional, (25)
"This house is actually better than the photos show. It has a beautiful view from the wrap around porch, vineyards all around. The location is great, feels far away but very close to town. We stayed as a family and it had everything we could have asked for. The recent remodel did not cut corners anywhere and paid much attention to detail. We look forward to stay again."
Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.
Property grounds
Healdsburg Cottage Walk to the Plaza, Workspace
10.0 out of 10, Exceptional, (203)
"We have stayed in Healdsburg before but this is our first time at this property. It won’t be our last. Great location- easy walk to the center of Healdsburg. Cottage is perfect size and amenities. Great hosts. Thank you!"
Healdsburg Cottage Walk to the Plaza, Workspace
Fridge, microwave, oven, stovetop
Beautiful Cottage overlooking vineyards. Three minutes from downtown!
10.0 out of 10, Exceptional, (212)
"Beautiful property in wonderful location. Great place to stay for our family while visiting Sonoma for a weddding!"
Beautiful Cottage overlooking vineyards. Three minutes from downtown!
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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

Front of property - evening/night
Hotel Trio Healdsburg
3.0 star property
9.4 out of 10, Exceptional, (641)
"Good quality for a fair price. "
The price is NZ$381
per night
20 May - 21 May
Hotel Trio Healdsburg
Courtyard
The Lodge at Healdsburg, Tapestry Collection by Hilton
3.5 star property
8.8 out of 10, Excellent, (125)
"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 NZ$318
per night
3 Jun - 4 Jun
The Lodge at Healdsburg, Tapestry Collection by Hilton
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, (1008)
"Room was comfortable and staff was grand."
The price is NZ$289
per night
15 May - 16 May
Best Western Dry Creek Inn
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Healdsburg holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Healdsburg. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Healdsburg. Seeing all the best attractions is bound to make you fall in love with Healdsburg. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Healdsburg short-term rentals, that won’t be hard to do.

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