Healdsburg Vacation Rentals

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Jul 2 - Jul 3
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Jul 3 - Jul 4
This weekend
Jul 4 - Jul 6
Next weekend
Jul 11 - Jul 13

Vacation Rentals in Healdsburg

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg
Outdoor pool

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

10.0 out of 10, Exceptional, (32)
"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
Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza
Outdoor pool, a heated pool

Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza

10.0 out of 10, Exceptional, (165)
"Fantastic and relaxing stay. Beautiful views, comfortable home, peaceful surroundings. Always an excellent place to recharge. "
Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza
Chalk Hill Cottage Close to Wineries
Exterior

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (37)
"The Chalk Hill cottage was the perfect getaway for Sonoma wine lovers. Located in Alexander Valley and close to great wineries."
Chalk Hill Cottage Close to Wineries
Wooded Restful Retreat, with broad scenic views, outdoor dining
Fridge, microwave, oven, stovetop

Wooded Restful Retreat, with broad scenic views, outdoor dining

10.0 out of 10, Exceptional, (306)
"Property is spotless. View is spectacular. Central location to restaurants and vineyards. Host was friendly and helpful! Highly recommend this property. "
Wooded Restful Retreat, with broad scenic views, outdoor dining
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (60)
"Great stay, recommend in every way"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!
Golf

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

9.6 out of 10, Exceptional, (167)
"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!
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
Dining

✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

10.0 out of 10, Exceptional, (294)
"We love staying at this cabin. It is peaceful, has a great location, and is the perfect place to unwind."
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
Vineyards Edge - Pool, Hot Tub, Bikes, Pets Welcome, Fire Pit- 1mi to Downtown
Terrace/patio

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

10.0 out of 10, Exceptional, (9)
"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
Healdsburg Home with Magnificent Vineyard View by RedAwning
Terrace/patio

Healdsburg Home with Magnificent Vineyard View by RedAwning

10.0 out of 10, Exceptional, (18)
"Had a great stay!"
Healdsburg Home with Magnificent Vineyard View by RedAwning
Secluded Vineyard Estate Healdsburg
A heated pool

Secluded Vineyard Estate Healdsburg

9.8 out of 10, Exceptional, (119)
"Nice experience"
Secluded Vineyard Estate Healdsburg
✨River View Lodge | Private River Access, Hot Tub, Kayaks & Views
Outdoor dining

✨River View Lodge | Private River Access, Hot Tub, Kayaks & Views

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. "
$1,038 nightly
The price is $1,153
Jul 6 - Jul 7
Total includes taxes and fees
✨River View Lodge | Private River Access, Hot Tub, Kayaks & Views
Cypress House & Studio, Walk to Healdsburg Plaza by RedAwning
Exterior

Cypress House & Studio, Walk to Healdsburg Plaza by RedAwning

9.8 out of 10, Exceptional, (25)
"House was super convenient to downtown Healdsburg and all the attractions including restaurants, bakeries, coffee shops, wine tastings, and shopping."
Cypress House & Studio, Walk to Healdsburg Plaza by RedAwning
Cozy vineyard studio in welcoming Healdsburg with WiFi, AC, fireplace, jacuzzi
Living area

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

Cozy vineyard studio in welcoming Healdsburg with WiFi, AC, fireplace, jacuzzi
Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.
Fridge, microwave, oven, stovetop

Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.

10.0 out of 10, Exceptional, (34)
"Outstanding property and location. Hosts were super helpful and the home was beyond our expectations."
Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.
4 BEDROOM plus PRIVATE DEN, 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
Terrace/patio

4 BEDROOM plus PRIVATE DEN, 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE

10.0 out of 10, Exceptional, (191)
"We stayed here for husband’s birthday weekend. Beautiful property. It had everything we needed for a relaxing weekend away. "
4 BEDROOM plus PRIVATE DEN, 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
Heron House--The River House in the Redwoods
Outdoor spa tub

Heron House--The River House in the Redwoods

10.0 out of 10, Exceptional, (23)
"We had a fabulous stay. Great house with a great location. It was lovely waking up and going outside to enjoy the river and woods around us. 5 min drive from Healdsburg main streets with great stores and restaurants. Enjoyed our drive to the coast, redwoods, and vineyards! Would stay again!"
Heron House--The River House in the Redwoods
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Smart TV, fireplace, DVD player, books

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

10.0 out of 10, Exceptional, (250)
"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
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
Outdoor pool, a heated pool

Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental

10.0 out of 10, Exceptional, (29)
"Great proximity to wine and town. Loved it! Leah is great"
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
Private Vineyard Haven--walk to the HBG Square!
A heated pool

Private Vineyard Haven--walk to the HBG Square!

9.8 out of 10, Exceptional, (58)
"The house was exactly as described. Lovely home and garden area. Perfect location to explore Healdsburg and surrounding area"
Private Vineyard Haven--walk to the HBG Square!
Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball
Game room

Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball

10.0 out of 10, Exceptional, (12)
"We had the best time at Bird & Barrel!! Every detail was thought through and the home was beautiful. The location was incredible, so close to town and wineries. We had the perfect weekend and can’t recommend it enough!!! We can’t wait to come back!"
Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball
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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Frequently asked questions

Are there vacation rentals in Healdsburg?

Yes, there are vacation rentals in Healdsburg near SingleThread Farm at Dry Creek, or you can choose a secluded option if you want 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's the top vacation rental that Healdsburg has to offer?

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg: This Healdsburg vacation home rental is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Healdsburg?

Expedia has 141 vacation 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 SingleThread Farm at Dry Creek are other places to visit while you're in town.

What are vacation rentals like in Healdsburg?

Vacation rentals are privately owned properties you can book for several days or more in Healdsburg. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.