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Compare 215 Vacation Homes in Healdsburg with updated reviews, rates, and availability.

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, (114)
"We spent Thanksgiving at Riverfront and it was perfect! The house was very clean and well stocked in every room. The decks with the view of the Russian River are amazing."
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
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, (231)
"We rented the Coop for 4 weeks and enjoyed all the amenities and the staff. Kristen was forever helpful and our gardener Luis was a delight. The space was kept immaculately clean and we had all that we needed and wanted. We have already booked for next year and plan to make it an annual trip."
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
~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, (63)
"It was nice There were no sheets for the pull out bed in sunroom One roll of paper towels is not enough Need more than two dish towels "
~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~
Wine Country Get Away
Room

Wine Country Get Away

10.0 out of 10, Exceptional, (23)
"Very nice"
Wine Country Get Away
Wooded Restful Retreat, with broad scenic views, outdoor dining
A view that lasts from first light to moonrise to sunrise.

Wooded Restful Retreat, with broad scenic views, outdoor dining

10.0 out of 10, Exceptional, (296)
"We really enjoyed our time in Healdsburg. The house was perfect! Very clean, comfy beds and close to town. Beautiful view off the back deck. Will rent again on our next trip to the area. "
Wooded Restful Retreat, with broad scenic views, outdoor dining
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
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, (164)
" 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!
Lazy Bear Lodge-Celebrate New Year's in a 5-Star Redwood Cabin! HotTub! WiFi
Twilight and all is right

Lazy Bear Lodge-Celebrate New Year's in a 5-Star Redwood Cabin! HotTub! WiFi

9.6 out of 10, Exceptional, (46)
"We’ve stayed in several rentals in Guerneville but this was one of our favorites to spend time with family. Can’t recommend it enough and hope to be back! Perfect amenities with everything we needed for a great weekend. Well stocked kitchen, cable TV, fireplace, AC/heat, grill, jacuzzi, office with monitor, board games, and plenty of bedrooms and bathroom. Beautiful location in the trees with a nice walking loop in the neighborhood for getting some steps in. Very friendly community. Short drive...
Lazy Bear Lodge-Celebrate New Year's in a 5-Star Redwood Cabin! HotTub! WiFi
The Sonoma Valley Cottage

The Sonoma Valley Cottage

9.8 out of 10, Exceptional, (6)
"Beautiful home with all we needed for our stay. Everything was spotless and we loved the outside patio. The only thing missing was a washer and drier. We noticed that the stoppers in the bathroom sinks were missing. We worried about dropping something down the drain. Maybe some blackout curtains in the master bedroom would be helpful. "
The Sonoma Valley Cottage
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!
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, (231)
"I highly recommend to stay here and eat at the recommended restaurants. We are 3 out of 7 of the recommendations in the house binder. The house is cozy, updated, immaculate and beautiful."
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
C - Wineries/breweries seconds away
Full sized kitchen stocked with everything you need to prepare a nice meal. Gas range dishwasher and side by side refrigerator with ice and water dispenser.

C - Wineries/breweries seconds away

9.6 out of 10, Exceptional, (11)
"This was nice location, right next to the highway 101. Check-in process was easy. Comfortable place to stay. However the pullout couch wasn't good quality - gave me back pain. It said, take trash out when leaving, but we weren't sure where to throw the trash bag. "
The price is SAR 485
SAR 623 total
includes taxes & fees
26 Dec - 27 Dec
C - Wineries/breweries seconds away
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
Vineyards Edge - Pool, Hot Tub, Bikes, Pets Welcome, Fire Pit- 1mi to Downtown
Bonus Room with Shuffleboard table

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

10.0 out of 10, Exceptional, (7)
"It is welcoming and lots of light! Very modern with great art! Feels like you are home, your own home, not someone else’s! And so quiet! I have stayed in many VRBO places but this was the best I have ever found! Loved it! "
Vineyards Edge - Pool, Hot Tub, Bikes, Pets Welcome, Fire Pit- 1mi to Downtown
Walk to Russian River - Casa Del Rio - Unit A
Outdoor dining

Walk to Russian River - Casa Del Rio - Unit A

9.4 out of 10, Exceptional, (24)
"It was very clean."
The price is SAR 563
SAR 1,551 total
includes taxes & fees
23 Jan - 24 January 2025
Walk to Russian River - Casa Del Rio - Unit A
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
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
4 Couples or 2 Families, Private and Prime Location, Pool and Hot Tub
Pool

4 Couples or 2 Families, Private and Prime Location, Pool and Hot Tub

9.8 out of 10, Exceptional, (56)
"Cc"
4 Couples or 2 Families, Private and Prime Location, Pool and Hot Tub
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

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

8.8 out of 10, Excellent, (18)
"This is a very solid property which we enjoyed quite a bit. The view is nice, the space was clean and quiet, and the hot tub worked. The layout was a bit hard to discern until we arrived, the two queen beds are in one structure with the bathroom, it would be close quarters for two adult couples but was great for us as just one couple, would be great for two separate individuals or a couple with kids. A couple reviews mentioned a smell in the living room, there was a bit of a stale odor but it...
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
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, (20)
"We spent Thanksgiving week at the home. Description of property is good. Lots of space for families to gather. Good access to groceries in Santa Rosa , good restaurants and wine tours. Outdoor space is ample "
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
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

✨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, (279)
"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 ✨
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, (231)
"We rented the Coop for 4 weeks and enjoyed all the amenities and the staff. Kristen was forever helpful and our gardener Luis was a delight. The space was kept immaculately clean and we had all that we needed and wanted. We have already booked for next year and plan to make it an annual trip."
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
Chalk Hill Cottage Close to Wineries

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (29)
"Location is excellent, property is clean and quiet, and hosts were very responsive. This is our second time at this cottage and look forward to staying here again. "
Chalk Hill Cottage Close to 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.