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Compare 203 Vacation Homes in Healdsburg with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (235)
"This house was perfect for a weekend with friends. The kitchen has everything you need and more! The dinning table and living area is very spacious and great to gather in. We had Ubers that cost 6-8 to get down to the square and nearing wineries. Excellent location and plenty of parking."
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

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

10.0 out of 10, Exceptional, (120)
"Loved the property, right on the water, very clean, well stocked for cooking in. Highly recommend.My only complaint is the laundry list of check out items… we were only there for a short weekend and had to launder all towels before leaving with incredibly specific instructions about cycle length and amount of detergent, etc. our checkout was at 11am… it was a little stressful to get it all done. if we’re paying a few hundred for a cleaning service, shouldn’t that include laundering towels? Or...
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country

Home near golf course, close to Healdsburg

10.0 out of 10, Exceptional, (28)
"Wow. We loved everything about this place. As comfortable as home. Fantastic location for lots of wineries. Windsor is a cute town. Nothing is very far. Best part was have a waffle maker to make our traditional Christmas morning waffles. Will definitely stay again. "
Home near golf course, close to Healdsburg

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

The Sonoma Valley Cottage

9.8 out of 10, Exceptional, (9)
"It was a perfect place for a bay area get away after the holiday. Easy location and access. I would recommend."
The Sonoma Valley Cottage

Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!

10.0 out of 10, Exceptional, (234)
"The home was wonderful and the property so relaxing and beautiful. We look forward to staying here again! Thank you so much Kristen for all your help as the property manager. "
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!

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

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: Prez Week Avail! 5-Star Cabin! HotTub! WiFi/Cabin Perfection

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: Prez Week Avail! 5-Star Cabin! HotTub! WiFi/Cabin Perfection

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

Private Sanctuary 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...
Private Sanctuary with private pond, pool and hot tub!

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!

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

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!

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

8.4 out of 10, Very Good, (21)
"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

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

9.8 out of 10, Exceptional, (22)
"We met up with our out of town family for the holidays at Reflections and it was perfect for us. It was very clean, the beds were comfortable, the hot tub was nice, and we really liked having the separate spaces which gave everyone plenty of room. We’d love to visit again when it is warm enough to use the pool."
~ Reflections. Hot tub, Pool, Main House + 3 Multiple Guest Cottages ~

Escape to Dry Creek Valley in Healdsburg in a Beautifully Renovated Farm House

Escape to Dry Creek Valley in Healdsburg in a Beautifully Renovated Farm House

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

10.0 out of 10, Exceptional, (28)
"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

Walk to Russian River - Casa del Rio - Unit B

9.4 out of 10, Exceptional, (13)
"We only stayed 1 night, but it fit our needs just fine. The unit is nicely laid out, updated kitchen and cozy beds. It was cold, but we had the heater. It would have been nice to have extra blankets for the living room or to use as throws. Also, coffee was available, but no creamer, just sugar. These are nice to haves of course, but overall the place is very nice and would be ideal for those coming to enjoy the river in the summer time. The deck is cozy and would be fun to hang out on a summer...
The price is AED 367
AED 1,299 total
includes taxes & fees
4 Feb - 5 Feb
Walk to Russian River - Casa del Rio - Unit B
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

4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views

10.0 out of 10, Exceptional, (144)
"Beautiful setting with a wonderful home. Loved the location near Healdsburg. Everything was convenient. The property manager was fantastic!"
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views

Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

10.0 out of 10, Exceptional, (347)
"Beautiful Pacific views, a very comfortable room and a meadow with deer and other wildlife; this is The Sea Ranch!"
Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard

9.8 out of 10, Exceptional, (414)
"This is the second time we have brought friends to the property. It is very clean and homey. We love sitting and watching the ocean, the fireplace was wonderful since it was cold outside. Walked on the beach and ate a few meals out. Looking forward to going back again, it is the perfect getaway!!"
Your Oceanfront Experience - Hot Tub - Lovely Fenced Courtyard
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.