Healdsburg Holiday Rentals

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Holiday Rentals in Healdsburg

Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

9.2 out of 10, Wonderful, (58)
"The cottage is a comfortable house. "
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

Wooded Restful Retreat, with broad scenic views, outdoor dining

10.0 out of 10, Exceptional, (312)
"The VRBO was exactly as described. Communication with Cynthia was fast and she answered all of our questions. The beds were super comfortable and place was spotless and exactly as described. Would definitely stay again!"
Wooded Restful Retreat, with broad scenic views, outdoor dining

Casa Pavone, by Vinifera Homes

10.0 out of 10, Exceptional, (7)
Casa Pavone, by Vinifera Homes

Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views

10.0 out of 10, Exceptional, (149)
"Wonderful house and yard. Manager is excellent as well. We love staying here"
Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

10.0 out of 10, Exceptional, (63)
"Great stay, recommend in every way"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

10.0 out of 10, Exceptional, (34)
"Absolutely wonderful stay. The house was beautiful and clean, with multiple spacious common areas for family time. The Limerick Lane team was also incredibly communicative and accommodating throughout. 100% recommend."
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

Magnolia Ranch Vineyards | Historic house in Healdsburg with lovely private yard

10.0 out of 10, Exceptional, (12)
"Comfy beds, great location & views. 1 mile from town - very peaceful and nice sized 2 bedroom home. Perfect for a coupes wine tasting. "
Magnolia Ranch Vineyards | Historic house in Healdsburg with lovely private yard

Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

10.0 out of 10, Exceptional, (257)
"Our group had a fantastic stay at this property. The location is amazing - minutes from downtown Healdsburg but just far enough to feel a bit secluded. Tons of great wineries nearby (I recommend De La Montanya)."
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!

9.6 out of 10, Exceptional, (168)
"Cool cabin, lots of communication with host. Hummingbirds were amazing, there were hundreds. Didn’t realize both bathrooms were on the lowest floor so the top floor bedroom had a two story walk down when facilities were needed. Roads are extremely narrow to get to house and we were expecting an easier route to the river. Great spot for folks looking for an “off the beaten path” stay. Treehouse feeling was great."
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!

Cozy vineyard studio in welcoming Healdsburg with WiFi, AC, fireplace, jacuzzi

"The studio was perfect for me and my pups. The kitchen was stocked with new utensils and cooking supplies. I had a chance to meet the hosts - I would have loved to have spent more time with them! Lovely people. But I’ll be back again to make that happen!"
Cozy vineyard studio in welcoming Healdsburg with WiFi, AC, fireplace, jacuzzi

Secluded Vineyard Estate Healdsburg

9.8 out of 10, Exceptional, (121)
"Nice experience"
Secluded Vineyard Estate Healdsburg

Vineyards Edge - Pool, Hot Tub, Bikes, Pets Welcome, Fire Pit- 1mi to Downtown

10.0 out of 10, Exceptional, (11)
"This was one of the most incredible VRBOs I have ever stayed at. Far exceeded every expectation and the hosts were so nice and communicative."
Vineyards Edge - Pool, Hot Tub, Bikes, Pets Welcome, Fire Pit- 1mi to Downtown

Xanadu Healdsburg | Luxury Estate in Healdsburg

10.0 out of 10, Exceptional, (26)
"We really enjoyed the pool and family room!"
Xanadu Healdsburg | Luxury Estate in Healdsburg

Rivers Breeze | Complimentary wine tasting at Croix included!

10.0 out of 10, Exceptional, (15)
"In Healdsburg to visit family and could not have had a more comfortable and lovely place to stay! It was impeccably clean, well located and so cute! We loved it!"
Rivers Breeze | Complimentary wine tasting at Croix included!

✨River View Lodge | Tasting at Croix included!

9.6 out of 10, Exceptional, (70)
"The property is perfectly located just 10 minutes from central Healdsburg. Great for wine tasting and family time. "
✨River View Lodge | Tasting at Croix included!

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

10.0 out of 10, Exceptional, (11)
"Ideal for a relaxing time in wine country! The winery on property is fantastic and highly recommend it!"
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

Stunning Dry Creek Road Estate

10.0 out of 10, Exceptional, (5)
"House was beautiful, property manager was super helpful throughout the process."
Stunning Dry Creek Road Estate

Santini Farmhouse | Complimentary tasting at Croix Winery included!

10.0 out of 10, Exceptional, (48)
"Everything was perfect"
Santini Farmhouse | Complimentary tasting at Croix Winery included!

Redwood River House--Complimentary wine tasting at Croix included!

9.4 out of 10, Exceptional, (63)
"Spent a few days here with some friends and their young children. The space was perfect for our visit and we loved the location!"
Redwood River House--Complimentary wine tasting at Croix included!

Private Luxury home in Healdsburg with Vineyard, Sauna, Hot tub, Tesla Charger

10.0 out of 10, Exceptional, (8)
"Stunning property! The perfect getaway for a girls weekend. "
Private Luxury home in Healdsburg with Vineyard, Sauna, Hot tub, Tesla Charger
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

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 top-notch restaurants and wineries.

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 143 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.