Holiday Homes in Healdsburg

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Featured Holiday Homes in Healdsburg

Wooded Restful Retreat, with broad scenic views, outdoor dining
10.0 out of 10, Exceptional, 281 reviews
"My Wife and I had a wonderful experience at this property. The home has everything you need. Great views and incredibly peaceful. Perfect spot."
Wooded Restful Retreat, with broad scenic views, outdoor dining
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, 82 reviews
"Stayed mid week for several days. Overall a very nice experience. Super clean and quiet!"
Cottage home near the Russian River; county parks; numerous wineries
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
10.0 out of 10, Exceptional, 92 reviews
"We went here with a group of friends and had the most amazing time! We will absolutely be going back. The house was really considered and had everything we needed. Also, can't beat being right on the water!"
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
~ Riverfront 3 Bedroom + hot tub, private dock & kayaks. 3/4 mile from town ~
10.0 out of 10, Exceptional, 48 reviews
"The home is beautiful, comfortable and well stocked. We enjoyed the dock, the hot tub and the lovely kitchen and dining areas. It was quiet and serene. Hope to return soon."
~ Riverfront 3 Bedroom + hot tub, private dock & kayaks. 3/4 mile from town ~
Valley Vista- Forest bungalow with valley views, dog friendly and hot tub!
10.0 out of 10, Exceptional, 59 reviews
"Beautiful home and very well appointed. The neighborhood was quiet and easy access walking to local shops. Lovely trees for tranquility in the back yard."
Valley Vista- Forest bungalow with valley views, dog friendly and hot tub!
Dog-friendly home in the redwoods with hot tub & amazing deck - steps to river
8.4 out of 10, Very good, 12 reviews
"The house was perfect for a family of 5. The beds were very comfortable."
Dog-friendly home in the redwoods with hot tub & amazing deck - steps to river
Fiano by AvantStay | Centrally Located Haven w/ Stunning Courtyard & Pool Table
9.4 out of 10, Exceptional, 11 reviews
"Hello, my family and I had a nice stay in Windsor while visiting from the Bay Area for our Dad's, memorial service. Unfortunately it was cut short by a nearby forest fire the smoke from which was able to come through a window that could not be closed (broken crank) and an internally installed A/C unit. Our daughter is respritorally challenged, so we chose to leave. Other than some loose fixtures and an ill-equipped kitchen, it was a nice, clean place and easy to hang out in. -James"
Fiano by AvantStay | Centrally Located Haven w/ Stunning Courtyard & Pool Table
Beautiful Cottage overlooking vineyards. Three minutes from downtown!
10.0 out of 10, Exceptional, 215 reviews
"We had a fabulous time during our 10 day stay in the Coop Cottage at Ru's Farm. Lele, our host, was absolutely wonderful! She was on top of every request and gave us excellent recommendations regarding activities and restaurants. The cottage is beautiful just like the photos on the listing page. It is perfect for two couples as it has two large bedrooms with king beds and ensuite baths. There is also a third very small bedroom with a queen and 1/2 bath. We will be back!!!!"
Beautiful Cottage overlooking vineyards. Three minutes from downtown!
Oak Leaf Retreat - 5 Acres, Spa & Vineyards! Peaceful.
10.0 out of 10, Exceptional, 100 reviews
"We wanted to stay in this home, this area, as we were visiting family who had some kids graduating. So we wanted to spend some time with family & the graduates. The place was spacious, the hosts were awesome. They answered any questions right away & were accommodating with any of our needs. The property was lovely & peaceful! The kitchen was well stocked with extras we might need. The house was decorated with lovely travel art & lots of bookshelves filled with awesome books. We did see a few...
Oak Leaf Retreat - 5 Acres, Spa & Vineyards! Peaceful.
Dry Creek Valley Home and Vineyard
10.0 out of 10, Exceptional, 42 reviews
"Absolutely BEAUTIFUL home and yard. It was exactly what we were looking for. If I could give it a 10 star I would!! Does not disappoint!!"
Dry Creek Valley Home and Vineyard
Riverfront, dog-friendly home with private hot tub, fireplaces & amazing decks
8.4 out of 10, Very good, 8 reviews
"This funky, spacious property was just perfect for two couples for a cycling holiday. We loved hanging out in all the social spaces, inside and out. The river was great to cool off in. The routes inland, south in the forests, and west to the coast are excellent for road biking. The gardens were beautiful & the fencing made parking & setting up the bikes secure. We appreciated the hot tub after one misty ride. We had no problems with rodents, since we kept all our food in the fridge. We had a...
Riverfront, dog-friendly home with private hot tub, fireplaces & amazing decks
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
7.6 out of 10, Good, 9 reviews
"We loved the location as it was close to everywhere we planned on visiting and it was nice to have a location with a hot tub to enjoy. The pillows were amazing! The problem with this location is that it is right across from a vineyard and it was harvest season and we got little to no sleep due to the ongoing activity. Workers were driving up and down the road with tractors and in the vineyard there were harvesters with spotlights so it was very busy. The cabin furniture could use some...
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country
9.8 out of 10, Exceptional, 19 reviews
"We loved this property! We did a mini high school reunion with friends from 40 years ago. The house was amazing and did not disappoint at all. We laid by the pool, played cards outside. Close to Healdsburg Square (7 minutes away). This trip was beyond all our expectations and the house was clean and big and the view was amazing. Recommend for a group of 8 or less. We will definitely book again!"
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country
Lovely Tudor Home w/ Pool & Spa near Russian River, short walk to Guerneville
9.8 out of 10, Exceptional, 116 reviews
"This was a lovely property! So quaint and adorable yet so much room for the six of us to have our own space. We'll be back for sure!"
Lovely Tudor Home w/ Pool & Spa near Russian River, short walk to Guerneville
B - Wine Country Getaway
9.8 out of 10, Exceptional, 11 reviews
"This was our first time staying at this property and my husband and I were very pleased. The pictures and description are 100% accurate. We loved having the added security of being gated in. Super easy with the code to enter and exit and we liked being able to park right next to our unit. Although near Highway 101, it was quiet and peaceful. Will definitely stay again!"
B - Wine Country Getaway
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat
10.0 out of 10, Exceptional, 17 reviews
"We celebrated our daughter's 16th birthday with a weekend in Healdsburg and stayed at Limerick Lane. The house was dreamy, the beds were notably more comfortable than our own, and the location was inspirational. We didn't want to leave! Would comment that the second bathroom is across the house from the secondary bedrooms. Was fine for our family, but might be challenging for some groups."
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat
Stylish Modern Farmhouse with Private Pool, Outdoor Kitchen, Game Room & WiFi
10.0 out of 10, Exceptional, 35 reviews
"We stayed with friends for 2 nights and we all enjoyed the house so much. I only have 2 issues, and they certainly are not deal breakers and I still give the property 5 stars, but it would have been nice to have a home instruction manual. We couldn't get the fireplace to work, not did we know there was a key to the pool house that had a peleton. It would have been nice to have had access to that room."
Stylish Modern Farmhouse with Private Pool, Outdoor Kitchen, Game Room & WiFi
Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining
10.0 out of 10, Exceptional, 1 review
"Great, communicative hosts and wonderful, close-in location with a rural setting and beautiful outdoor area. Well appointed house. We had a fantastic time for our college friend annual reunion trip."
Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining
Guerneville Getaway: Craftsman Retreat! Hot Tub! WiFi! Fun Game rm! Wineries
9.6 out of 10, Exceptional, 5 reviews
"Beautiful surroundings and neighborhood"
Guerneville Getaway: Craftsman Retreat! Hot Tub! WiFi! Fun Game rm! Wineries
Flora Vina - Country Home with Vineyard Views
10.0 out of 10, Exceptional, 3 reviews
"great place for a month escape!"
Flora Vina - Country Home with Vineyard Views
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See all available properties in Healdsburg
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.

Other property types in Healdsburg

Dry Creek Cottage - Healdsburg
9.8 out of 10, Exceptional, 132 reviews
"We enjoyed our stay immensely! The hosts were so welcoming and kind. The cottage was peaceful, secluded, a great size, and had everything we needed. The pool was lovely and the location was the perfect distance from downtown. Very pleased we were able to book this spot!!"
Dry Creek Cottage - Healdsburg
Chalk Hill Cottage Close to Wineries
9.8 out of 10, Exceptional, 16 reviews
"We loved our cottage. Very well appointed, furniture lovely, kitchen cute. A little dark because it's set into hill but fine with lights on. We'll go back."
Chalk Hill Cottage Close to Wineries
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
10.0 out of 10, Exceptional, 148 reviews
"We love staying at this property in Dry Creek! It is so clean and has everything you'd want.. the location is perfect, right in the middle of everything Dry Creek and Healdsburg."
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.

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