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Check prices for these dates

Next weekend
31 Muh. - 2 Saf.
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7 Saf. - 9 Saf.
In one month
21 Saf. - 23 Saf.
In two months
21 Rab. I - 23 Rab. I

Compare 210 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, (233)
"We have stayed in properties in many cities. This is one of the finest we have ever experienced. We could not ask for a better vacation home. MMichael "
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
Pool

5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

9.8 out of 10, Exceptional, (22)
"We loved our 2-night stay. We especially loved that each person in our group had their own bedroom (and bathroom). The house is beautifully designed with comfortable beds and couches. The living/dining room has gorgeous massive ceilings. We also loved the huge dining table for meals/games, etc. The aesthetic throughout the house was right up the alley of our group. Everything you need is provided and has been thoughtfully curated. Every room was well-appointed and very clean.The hot tub...
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
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, (119)
"This is a really well designed and maintained property (considering the flood plane can occasionally bring water up to the street level) right on the river. Our band was looking for a place to do a little retreat and this fit the bill. You will see that all of the house rules align with Sonoma county regulations for vacation properties and it's not a big deal. The interior of the house is really well insulated thermally and acoustically. (I was hanging out in the hot tub while the band was...
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
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
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, (92)
"Property was perfect for me while I was taking care of my grandchildren"
Cottage home near the Russian River; county parks; numerous wineries
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, (233)
"This is the perfect place to stay if you want the quiet beauty of the vineyards but the proximity to downtown. Since we were a group of two couples it was really lovely to have two ensuites with king beds. Don’t forget your swimsuit as it’s nice to take advantage of the hot tub, especially at sunset with a glass of wine in your hand."
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
The Sonoma Valley Cottage

The Sonoma Valley Cottage

9.8 out of 10, Exceptional, (7)
"The house was perfect for our family. It was well equipped and very clean and tidy. We had a great time."
The Sonoma Valley Cottage
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!
Plenty of room for your whole crew to board game and sip the night away.

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

9.6 out of 10, Exceptional, (165)
" Place is a real gem: Beautiful views of the Russian River valley from the house and from several decks; Spacious and comfortable inside; Hot tub outside on deck with beautiful view of the valley; easy walk to water. We also did some nearby hikes and spent time in the lovely town of Healdsburg. Owner Stephen and manager Tenay were great hosts."
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country

Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country

10.0 out of 10, Exceptional, (24)
"Beautiful home with beautiful pool and hot tub. Had the best time. Close to Healdsburg and many wineries. Strongly recommend "
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country
Lazy Bear Lodge: Presidents' week avail! 5-Star Cabin! Hot Tub! WiFi
Twilight and all is right

Lazy Bear Lodge: Presidents' week avail! 5-Star Cabin! Hot Tub! WiFi

9.6 out of 10, Exceptional, (49)
"We had a lovely time here! Cozy, big gas fireplace in living room, comfy thick mattresses, nice hot tub. House is in a little hilly neighborhood, but once you’re inside the house you would never know anyone else was around you. The property is beautifully and cleverly landscaped for privacy, and the back of the house backs up to a lush and woodsy hillside. Very green, shady and pretty. Near to town and the redwoods. We would return for sure. "
Lazy Bear Lodge: Presidents' week avail! 5-Star Cabin! Hot Tub! WiFi
B - Wine Country Getaway
King sized bed with tempurpedic mattress and sofa with a pull out bed for R&R.

B - Wine Country Getaway

9.6 out of 10, Exceptional, (24)
"Really easy to get to, clean, and quiet! People booking: make a note of the letter used in the title of your stay. That is the house number you will stay in. Didn’t put that together until long after we got there. Otherwise we had to guess which place was ours by which door the code unlocked."
The price is SAR 446
SAR 579 total
includes taxes & fees
30 Jan - 31 Jan
B - Wine Country Getaway
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!
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, (33)
"We had a great time in this home it was beautiful and spacious, we hope to return someday!"
Windsor home on golf course w/ hot tub
3 units with private pond, pool and hot tub!
Pool

3 units with private pond, pool and hot tub!

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a fantastic stay at Lily Pad Ranch! This was our second time and the property is just as spectacular as we remembered it; it remains our favorite rental. The well appointed house and spacious guest house are embedded in super-private and serene landscaping. The icing on the cake is the beautiful lake with its walking path and floating gazebo. Very romantic! Additionally there is a large pool area with integrated Spa, a fire pit, ample seating and chaises for lounging. Most of our time...
3 units with private pond, pool and hot tub!
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!
Main house

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

10.0 out of 10, Exceptional, (26)
"The property is amazing and even better than advertised. Location is great for exploring Healdsburg and surrounding area. Our group of friends had a terrific time over new years and wouldn’t hesitate to return. Thank you!"
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!
Casa de la Esperanza: 1890s Historic Gem - 6BD/4BA

Casa de la Esperanza: 1890s Historic Gem - 6BD/4BA

9.8 out of 10, Exceptional, (8)
" The property was amazing. Huge backyard with lots of games to play. The older kids spent lots of time playing chess with the giant set. The hosts were very attentive and made sure our stay was the best it could be. Would definitely go back!!"
Casa de la Esperanza: 1890s Historic Gem - 6BD/4BA
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Pool

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

10.0 out of 10, Exceptional, (56)
"Our stay at this VRBO property was absolutely fantastic – truly a 10/10 experience! From the moment we walked in, it was clear that the home was designed with guests in mind. It didn’t feel like we were staying in someone else’s personal space; instead, it felt like a beautifully curated retreat made just for us. Every detail was thoughtfully considered. The house was spotless and had all the important amenities you’d want in a home away from home – a well-equipped kitchen, comfortable beds,...
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

8.6 out of 10, Excellent, (20)
"The place and weather was perfect. The house was clean, organized and had plenty of towels. I love the jacuzzi. The neighbors were really nice. I am a computer person and the wifi was off and on but ita ok, its good to have some nature time also. "
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
“Winetopia” Windsor Getaway - 34 Exceptional Reviews!
Interior

“Winetopia” Windsor Getaway - 34 Exceptional Reviews!

10.0 out of 10, Exceptional, (36)
"This place was so lovely and Nicole was awesome to work with! 6 Adults stayed here and everyone enjoyed their stay. The place was well appointed, beds and bedrooms were very comfortable. Outdoor area was spectacular. Close to everything you might need, grocery stores, walking trails, wineries! Would recommend this in a heartbeat. Thanks for helping us create wonderful memories!"
“Winetopia” Windsor Getaway - 34 Exceptional Reviews!
Heart of Wine Country, Cute Cottage w/Hot Tub
Creekside Oasis

Heart of Wine Country, Cute Cottage w/Hot Tub

9.8 out of 10, Exceptional, (19)
"We did a short visit over the new year holiday, went wine tasting and into Healdsburg for dinner. Lyft rides were abound and the home was a great landing spot for us. We enjoyed a dip in the hot tub and the gas fireplace was lovely. "
The price is SAR 994
SAR 2,059 total
includes taxes & fees
27 Jan - 28 Jan
Heart of Wine Country, Cute Cottage w/Hot Tub
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, (233)
"We have stayed in properties in many cities. This is one of the finest we have ever experienced. We could not ask for a better vacation home. MMichael "
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
✨Enjoy cooking together in the kitchen ✨

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

10.0 out of 10, Exceptional, (280)
"Charming cabin among the vineyard. Very comfortable, host is very informative. Love the location close to Healdsburg. This was our second visit, we hope to return again."
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
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, (154)
"My family and I stayed here for the Thanksgiving holiday and had an absolutely wonderful stay. The place is well equipped and very cozy with a wood burning fireplace, beautiful outdoor spaces (including multiple fire pits) and comfortable bedrooms. The host is also amazing - communication before, during and after was easy and included fantastic recommendations. And to top it all off, they even treated my family and I to a complimentary tasting at a local winery. Would definitely recommend!"
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
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.