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Compare 219 Vacation Homes in Healdsburg with updated reviews, rates, and availability.

Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Bliss House Panorama View 1

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

10.0 out of 10, Exceptional, (228)
"We had an amazing stay at this house! The location was ideal—close to everything in town, making it so convenient to explore. The house itself was spotless, beautifully maintained and stocked with everything you could possibly need. It felt like a true home away from home. The property manager was incredibly responsive and thorough, making the entire experience seamless and stress-free. We couldn’t recommend this place more—it’s perfect for anyone looking for a comfortable, well-equipped and...
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
Enjoy lawns, gardens, and a walk in through our vineyards

Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!

10.0 out of 10, Exceptional, (230)
"Just like the pictures. Grounds were gorgeous & the stay was very relaxing. My family had a wonderful time. "
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
The Sonoma Valley Cottage

The Sonoma Valley Cottage

9.6 out of 10, Exceptional, (5)
"Cool place. Place as easy to use. Lots of space inside"
The Sonoma Valley Cottage
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!

Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!

10.0 out of 10, Exceptional, (23)
"An incredible weekend. We absolutely loved our stay and this was the perfect place for our family to celebrate a big milestone birthday!"
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
The front of the house

Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country

10.0 out of 10, Exceptional, (112)
"Our group thoroughly enjoyed staying at Riverfront. From the adult-themed treehouse, we explored many of the natural wonders of the area - from the trees to the sea! Riverfront was very clean, well equipped, and communication with Charlie was excellent. It was close to feeling like home, with spectacular views of the Russian river and the surrounding forest. Highly recommend! "
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
Luxurious Large Home, Beautiful Pool, Extensive Gardens
Large ranch-style home, 40-foot pool with full sun

Luxurious Large Home, Beautiful Pool, Extensive Gardens

9.8 out of 10, Exceptional, (142)
"Spent a weekend here with family and friends. The vacation home is beautiful and very tastefully done! Offers spectacular views from front yard and backyard, and lots of entertainment with the game room and swimming pool. David is a warm and welcoming host, very easy to communicate with. We had a great time, and would definitely recommend this vacation home to those visiting the area!"
Luxurious Large Home, Beautiful Pool, Extensive Gardens
Hidden Oasis ~ a Private Luxury Home in Healdsburg

Hidden Oasis ~ a Private Luxury Home in Healdsburg

10.0 out of 10, Exceptional, (23)
"This home was perfect for our small group of friends who wanted a comfortable and very well appointed place to relax after a day of wine tasting. Don't let the rather plain exterior fool you - the inside is lovely, the beds are comfy, a the outside areas are perfect places to hang out. We enjoyed our stay very much and would definitely stay again!"
Hidden Oasis ~ a Private Luxury Home in Healdsburg
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
First Crush Cottage

Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

10.0 out of 10, Exceptional, (153)
"The cottage and the grounds are absolutely gorgeous! We loved the way the cottage was decorated, so cozy! Everything was well appointed. There are multiple places on the grounds to sit and enjoy a glass of wine and the scenery. It is the perfect size for two couples. The location is close to downtown Healdsburg, Dry Creek wineries and a five-minute walk to the Dry Creek General Store! Napa is only a little over an hour away. The owners and property manager responded quickly when we had...
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
4 Couple or 2/3 Families, Private w/Fantastic location, Views + Pool + Hot Tub
Pool

4 Couple or 2/3 Families, Private w/Fantastic location, Views + Pool + Hot Tub

9.8 out of 10, Exceptional, (55)
"We thoroughly enjoyed our stay here! Was a beautiful location"
4 Couple or 2/3 Families, Private w/Fantastic location, Views + Pool + Hot Tub
~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~
Enjoy the river life from your own private dock! Often open May - October.

~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~

10.0 out of 10, Exceptional, (61)
"Our family of four stayed at Paradise for the long weekend. The home was easy to check-in and immaculate. The beds were very comfortable, kitchen was well stocked, and we had access to kayaks and paddle boards. The view of the river was beautiful. The location was great. We were just minutes from delicious restaurants and enjoyed hiking in nearby Armstrong Redwoods and the Jenner Headlands Reserve with breathtaking views of the ocean. The host was excellent. Informative, organized, and...
~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~
Winemaker’s Fabulous Sonoma Wine Country Home
Dining

Winemaker’s Fabulous Sonoma Wine Country Home

10.0 out of 10, Exceptional, (65)
"The property was clean, quiet, and the communication with the managers of the property was exceptional. I rent a lot of properties and this one felt like coming home. Central location near the winery I run that made for a high level of convenience. "
The price is AED 911
AED 1,785 total
includes taxes & fees
24 Dec - 25 Dec
Winemaker’s Fabulous Sonoma Wine Country Home
~ Reflections. Hot tub, Pool, Main House + 3 Multiple Guest Cottages ~
Exterior

~ Reflections. Hot tub, Pool, Main House + 3 Multiple Guest Cottages ~

10.0 out of 10, Exceptional, (19)
"This was the perfect property for a weekend getaway with a group of six friends. The three little cabins provided convenient privacy, while the house was enough space for us all to come together and eat, hold classes, and write in a cozy setting. The only issue we ran into was the rogue gas fireplace in the living room, which seemed to have a mind of its own when it came time to turn it off. When it became too hot, we compensated with opening the windows and using the provided fan with no...
~ Reflections. Hot tub, Pool, Main House + 3 Multiple Guest Cottages ~
Villa Eileen: Riverfront Gem w/ Outdoor Kitchen & Private Beach

Villa Eileen: Riverfront Gem w/ Outdoor Kitchen & Private Beach

8.8 out of 10, Excellent, (16)
"Great private beach on the Russian river, across the river from Stumptown Brewery. Close to town, close to breweries and wineries. Korbel winery was a nice treat. Swimming to Stumptown brewery with the dog was pretty epic. Guerneville a small quaint town did not disappoint, eateries and a super market for all your grocery needs. "
Villa Eileen: Riverfront Gem w/ Outdoor Kitchen & Private Beach
Peaceful Windsor Retreat w/ Private Hot Tub!
Windsor Vacation Rental | 3BR | 2BA | 3 Steps Required for Entry

Peaceful Windsor Retreat w/ Private Hot Tub!

10.0 out of 10, Exceptional, (12)
"This is a great rental. Have stayed here twice now. It is perfectly situated in the heart of wine country. Close to stores too. House is beautiful spacious. . "
Peaceful Windsor Retreat w/ Private Hot Tub!
Home near golf course, close to Healdsburg
Living area

Home near golf course, close to Healdsburg

10.0 out of 10, Exceptional, (27)
"Great house and location"
Home near golf course, close to Healdsburg
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
Your vacation oasis awaits...

Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental

10.0 out of 10, Exceptional, (24)
"We have stayed in A LOT of VRBOs over the years, and this property was by far the best. The house itself is beautiful and full of meaningful touches (e.g., nice bath gels, fragrances, hangover meds, clothes steamer, pool towels, etc.) The yard and pool area are off-the-charts cool. We loved the heated pool and fire pits so much that we opted to spend our evenings there instead of paying to go elsewhere. And the location is perfect for those who want to be in the middle of wine country AND within...
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
Windsor home on golf course w/ hot tub
Outdoor spa tub

Windsor home on golf course w/ hot tub

9.6 out of 10, Exceptional, (31)
"Great location, nicely furnished and decor. Property was as described and good communication with host. The 1 thing we would recommend is your cleaning service needs to be a bit more thorough, the tubs were draining slowly due to hair clogging the drain which we cleaned out."
Windsor home on golf course w/ hot tub
Redwood River House--Serene Riverfront Cottage ­ In Healdsburg, Views, Kayak

Redwood River House--Serene Riverfront Cottage ­ In Healdsburg, Views, Kayak

9.4 out of 10, Exceptional, (61)
"My best friend and I (plus my dog) very much enjoyed this property. Conversation with the rental company was top notch. The two bedrooms and bathroom were clean and comfortable. The kitchen had everything we need to cook meals after enjoying the river all day. It could use a few more staples (oven mitts, aluminum foil, saran wrap, a few pieces of tupperware) but otherwise really great. The upper deck is lovely for bird watching and the lower level concrete slab by the river was perfect for...
Redwood River House--Serene Riverfront Cottage ­ In Healdsburg, Views, Kayak
Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach

Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach

9.8 out of 10, Exceptional, (25)
" If you’re looking for a clean, comfortable and quiet getaway in the woods, this is it. We enjoyed a three day getaway with our 1 yr old granddaughter and had a blast at the home and surrounding area…and so did our little dog who loved exploring the fenced yard. Big screen tv, good wifi, convenient in-suite laundry facilities, comfy bedrooms, clean bathrooms, well stocked kitchen… all made for a very enjoyable stay."
Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach
Cottage home near the Russian River; county parks; numerous wineries
Dining

Cottage home near the Russian River; county parks; numerous wineries

10.0 out of 10, Exceptional, (91)
"The property was very good and met all our needs with a couple of exceptions. The bathroom towels were not good, a little smelly and really need to be upgraded along with the toilet paper!"
Cottage home near the Russian River; county parks; numerous wineries
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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Other property types in Healdsburg

Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
Bliss House Panorama View 1

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

10.0 out of 10, Exceptional, (228)
"We had an amazing stay at this house! The location was ideal—close to everything in town, making it so convenient to explore. The house itself was spotless, beautifully maintained and stocked with everything you could possibly need. It felt like a true home away from home. The property manager was incredibly responsive and thorough, making the entire experience seamless and stress-free. We couldn’t recommend this place more—it’s perfect for anyone looking for a comfortable, well-equipped and...
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
B - Wine Country Getaway
King sized bed with tempurpedic mattress and sofa with a pull out bed for R&R.

B - Wine Country Getaway

9.4 out of 10, Exceptional, (20)
"This place was as advertised. Fairy small, but exactly what we expected. The laundry is shared. Location was great for what we were looking for; close to wineries and close to any amenities that towns offer."
The price is AED 437
AED 511 total
includes taxes & fees
3 Dec - 4 Dec
B - Wine Country Getaway
Newly Refurbished! Nest Cottage at ru's Farm.
Exterior

Newly Refurbished! Nest Cottage at ru's Farm.

9.8 out of 10, Exceptional, (156)
"This property is exactly as promised. It’s located in such a beautiful area of Healdsburg. If you’re looking for a quiet getaway this is the place for you!"
Newly Refurbished! Nest Cottage at ru's Farm.
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.