Search Vacation Homes in Healdsburg

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 210 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, (117)
"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
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
Lazy Bear Lodge:Celebrate MLK and Pres! 5-Star Redwood Cabin! HotTub! WiFi
Twilight and all is right

Lazy Bear Lodge:Celebrate MLK and Pres! 5-Star Redwood Cabin! HotTub! WiFi

9.6 out of 10, Exceptional, (48)
"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 MLK and Pres! 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
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
~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~
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, (232)
"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!
Wine Country Get Away
Room

Wine Country Get Away

10.0 out of 10, Exceptional, (23)
"Very nice"
Wine Country Get Away
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!
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 AED 474
AED 609 total
includes taxes & fees
6 Jan - 7 Jan
C - Wineries/breweries seconds away
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 AED 551
AED 1,506 total
includes taxes & fees
4 Jan - 5 Jan
Walk to Russian River - Casa Del Rio - Unit A
Casa de la Esperanza: 1890s Historic Gem - 6BD/4BA

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

9.8 out of 10, Exceptional, (7)
"We had a group of 12 ranging in age from 12 to 93 and we all had a wonderful time. The kitchen was well stocked and accommodated multiple cooks for an extensive dinner. The indoor and outdoor games were enjoyed by all ages. The common area was large enough for everyone to enjoy time together, without being cramped or constraining. The front veranda was such a pleasant place to hang out with our morning coffee. The back yard and rear deck had so much available to do that we never got a...
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
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, (21)
"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
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
Valley Vista- Forest bungalow with valley views, dog friendly and hot tub!

Valley Vista- Forest bungalow with valley views, dog friendly and hot tub!

10.0 out of 10, Exceptional, (73)
"Peaceful, quiet and clean. The house and property are very nice and very private and secluded. We had a very enjoyable stay!"
Valley Vista- Forest bungalow with valley views, dog friendly and hot tub!
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, (23)
"Clean property, secured by a gate with a code. 3 or 4 units on the property. Water pressure was a bit low, otherwise a perfect spot in between Healdsburg and Windsor. Just off the Arata Ln exit. This was my second time staying here. I would definitely book it again."
The price is AED 437
AED 567 total
includes taxes & fees
6 Jan - 7 Jan
B - Wine Country Getaway
Riverfront Cabin only 10 min from Plaza!
Main level living room

Riverfront Cabin only 10 min from Plaza!

10.0 out of 10, Exceptional, (8)
"Cute little rustic river cottage, stunning landscape and views of the Russian River, everything you need to get away for a few days and a great base to operate from as you indulge the Healdsburg food and wine scene"
Riverfront Cabin only 10 min from Plaza!
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, (18)
"Great place to stay in Windsor. Very clean and well stocked with towels, coffee and beautiful wine glasses to enjoy the wine we picked up at the wineries. Close to town. "
The price is AED 1,084
AED 2,150 total
includes taxes & fees
6 Jan - 7 Jan
Heart of Wine Country, Cute Cottage w/Hot Tub
Secluded Valley Retreat
Exterior

Secluded Valley Retreat

10.0 out of 10, Exceptional, (105)
"This is a spacious calming house about 18 minutes from downtown Healdsburg. We spent a hot weekend lounging, wine tasting and catching up in the pool at 9am (!) drinking our morning coffee. Beds are very comfy and the kitchen has all the tools you need to cook at home. Would think ahead about any evening transportation to downtown esp if you need a designated driver. The last mile to the house is dark and not easy to find. Otherwise a perfect home for a long weekend getaway. Thanks Danielle!!...
Secluded Valley Retreat
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.
Don't see what you're looking for?
See all available properties in Healdsburg
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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, (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 ✨
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
Chalk Hill Cottage Close to Wineries

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (30)
"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.