Head down to the beautiful town of Healdsburg in Sonoma County, California. The region is famed for its wineries, cuisines, star restaurants, top end hotels, luxury resorts, historic architecture as well as deep history and rich culture. Whether it is about visiting Healdsburg 19th-century plaza, exploring the century-old museum, enjoying sips of the wineries’ finest drinks or even just playing the local favorite Bocce ball, the small town has just the treat for you. You will have a fun time while you unwind during your vacation. Check out the following top 10 Vrbo accommodations in Healdsburg, that you can choose from while in town.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 13, 2023.
1. Luxurious country cottage in the hills (from USD 235)
Check out this quaint relaxing cottage offering a unique sense of rustic elegance in the heart of Chalk Hill Appellation. This one-bedroom one-bathroom cedar and stone cottage comfortably accommodates four guests. Relax in the evening outside by the gas fire pit under the cedar pergola and enjoy the panoramic scenery of the highland’s landscape. Highlights include television, internet connection, and parking space availability.
Top guest reviews
Amenities & Room:
Cottage is spacious enough comfortable and cozyThe bathroom is not real large and the door is off of the bedroom 6 - Would you go back?and it is fine for e-mail and the likeThe house is perfectly spacious and includes all the amenities anyone could want JohnWas a great base to do some Sonoma bike rides from Windsor and Healdsburg and wifi works great to stay in touch with the outside worldCleanliness:
Tastefully decorated clean and a great locationSuper clean and quaint Easy access to winerys all overThe cabin was clean and very comfortable would definitely stay againHost:
John is helpful and responsiveJohn was easy to communicate with friendly and even brought us sugar when we ran outJohn was very helpful and he personally brought additional coffee to usPrivate cottage with all the amenities great communication from host clear instructionsYes absolutely The owner was very helpful and we appreciate his responsivenessRead more reviewsLocation:
And a relaxing evening on the patio at Chalk Hill Cottageit's only a 15 minutes drive to the house )Great central location to go wine tasting and still being close to the 101 fwy to get around easily Beautiful propertyOf course there are many excellent wineries in close proximityThe location overall was also wonderful for us since it's just minutes from Windsor also easy to get on 101 to Healdsburg or other locations
2. Private cottage with swimming pool (from USD 295)
Dry Creek Cottage is a vineyard home overlooking great picturesque views. This private one-bedroom, one-bathroom cottage with a fireplace, fully equipped kitchen and a large pool is conveniently located near many excellent restaurants. The compound receives a lot of sun during the day, allowing you to lounge poolside on the large outdoor deck. You may fancy barbecue or cooking meals in the house’s large modern kitchen.
Top guest reviews
Amenities & Room:
The place is very comfortable and has everything you needThe cottage was clean and comfortable with a well stocked kitchenThe cottage was well-stocked and furnished and plenty spacious for our party of 3Enjoyed everything about the cottagebut we new that ahead of time and was not an issue for usCleanliness:
The pool and jacuzzi were refreshing and restoring after our raceThe owners were lovely and accommodating and the cottage was just as describedHost:
Rich and Joyce greeted us when we arrived and provided us with wonderful recommendations for our stayThey are so cute and sweetwere kind friendly and helpful hostsThe pool and jacuzzi added to our relaxing getaway Richard and Joyce were so friendly and helpfulpool and hot tub were niceRead more reviewsLocation:
but we really loved Rich and JoyceThe location is perfect 5 minutes from Healdsburg town and close to the dry Creek wine route and vineyardsThe location is great and super convenient though does require a vehicle or UberThe location was very convenient and close to townLoved the town and this property is the perfect distance in between Healdsburg and the Dry Creek Valley vineyards
3. Charming two-bedroom accommodation (from USD 584)
Located at the heart of Dry Creek Valley is this renovated, charming modern cottage surrounded by spectacular vineyards. This two-bedroom two-bathroom haven accommodates four guests. There is a king-size bed in one bedroom and a double bed in the other with each having a private bathroom. This stunning home features well-crafted interior decor, stunning sparkling well-equipped kitchen and an immaculately trimmed outdoor resting area well furnished for evening relaxation and gazes at the panoramic views. Suitably situated, it offers access to top wineries and restaurants. The cottage also includes a complimentary tasting at the world-renowned winery - Lambert Bridge.
Top guest reviews
Amenities & Room:
the kitchen is stocked with cooking supplies and the bathrooms are roomy and tastefully updatedthe pictures do no do it justiceThe cottage has everything you'll need is clean and well stockedThe property is meant for two couples looking to have a great home base with views to bootKim was an excellent point of contact during our stay and very accommodating to our inquiriesHost:
She is very accommodating and very responsive to requests for informationThey are wonderful top notch hostsKimberly was super easy to work with and responsiveThe owner has thought of everything and we appreciated her thoughtfulness and kindness in helping to make our weekend specialthe fire pits and the bbqRead more reviewsLocation:
The location was amazing and convenient to Healdsburg and the surrounding wineriesRight in the heart of beautiful Dry Creek Valley and minutes from picturesque HealdsburgFirst Crush is top notchFirst Crush is only 2 minutes from the Dry Creek General StoreBeautiful grounds lovely home great location for a relaxing stay in wine country
4. Private luxury stay with pool (from USD 925)
This elegant three-bedroom, two-bathroom luxury cottage offers a spectacular view of the Russian River Valley vineyards. Enjoy the comfort provided by the spacious living area with provisions of a television and stereo system for entertainment, the kitchen provides all basic cookware for meal preparation and the swimming area is perfect for relaxation during the hot summer days. Accommodating up to six guests, you can have fun playing outdoor Foosball on the deck or classic French Petanque on the court nestled between vineyard and pool.
Top guest reviews
Amenities & Room:
so many amenities only downfall was the shower in the master bedroomGreat view across the road and an open floorplan with room for 6 people all with functional living room and kitchen appliancesWe pretty much could not use the indoors until late evening after the sun went down While the cows are quaint if you have to leave the windows open to sleepThe large deck off the living room/dining room has a gas grill table for 6 comfy chaise lounges just steps from the poolcooking in the well-stocked kitchen and exploring the area with my cameraHost:
The owner is helpful and accommodating and made us feel very welcomeThe owner was great to work with throughout the process When we arrivedThe home is very well maintained with high quality touches yet rustic charmHouse needs some major work One bath was so tiny and smelled of urineOpen well decorated cottage with well equipped kitchenRead more reviewsLocation:
The location is perfect for exploring Sonoma County and wine tastingThis house is in a great location for wine countryVery good location near town and some of the best wineriesIt's a great place to stay since it's 5-10 minutes from hundreds of wineries and restaurantsVineyard Vista is the perfect location
5. Lavish vineyard home (from USD 365)
Check out this vineyard home located on the hilltop sits this modern two-bedroom one-bath guest house. It comfortably accommodates six guests. The two sparkling bedrooms have queen-size beds, the well-equipped kitchen with granite counters comes complete with all the accessories to prepare your favorite meals and an outdoor grill for barbecue sessions. Highlights include a large spa, access to swimming pool, Wi-Fi connection and lots of options for entertainment like board games, television and many more.
Top guest reviews
Amenities & Room:
The beds were very comfortable and the cool air at night meant we could sleep with the windows openThere were 4 of us- plenty of room and well equippedProbably the most beautiful view in Sonoma CountyIt is tucked away in the most beautiful lush forest and feels like your own private vineyard(we did dinner one night in town and one night at the Villa)Cleanliness:
100% (and more)The villa was beautifully appointed clean and in a very private location with gorgeous 360 degree viewsEverything was comfortable and relaxing and QUIET(we were supposed to go with another couple who couldn't after the fact) and was equipped enough to make some meals at the house too which we love to do when we rent Excellent spotHost:
New well appointed good instructionsOur hosts were gracious and very informative about the area and things to doThe cool evening also made for a wonderful hot tub dipWe appreciate their attention to our stay and warm welcomeGreat location and private feel made for great long weekendRead more reviewsLocation:
This is a perfectly sized and located home which provides easy access to great wineriesIt also was the Perfect setting close to many vineyards but tucked away from it all with breathtaking views10 min scenic drive from Healdsburg town square private hot tub at the rear of the house for star gazing so many great wineries within a very short drivebut it made for a very relaxing time Close to all the wineries we planned to visitDry Creek Villa is in the perfect location - far enough to get away from it all and close enough that can enjoy town as if you are staying there
6. Beautiful hideaway for two (from USD 325)
Located 10 minutes away from the historic Healdsburg square is this simple and pristine studio rental. The studio is best suited for a couple traveling as it can accommodate two guests. It includes a spacious full bathroom, a comfortable large queen bed, kitchenette which is well stocked and a well-lit cozy sitting area with television. The home is situated close to class restaurants, upscale shops, and wine tasting rooms.
Top guest reviews
Amenities & Room:
the bed is comfortable and there is A/C and fan to keep the room cool in hot weatherThere are also bottles of water in the fridgeIt was clean and cozyHost:
She and husband Bill are gracious hoststhe hostess and host are the kindest and most hospitable peopleA very sweet and helpful coupleYou can also do day trips to other areasHost are very helpful with trip planning Thanks LindaRead more reviewsLocation:
The property is located a quick and beautiful 5 minutes from downtown Healdsburg andJust a few miles west of HealdsburgLooking for some peace and tranquillity?The location is amazing Off a quiet road with nice walking biking or running Just a few miles from downtown Healdsburg and a great home base to visit all the Healdsburg wineriesIt's away from the crowd and feels secluded but a very short and easy drive to Healdsburg downtown
7. Mountain-top family retreat (from USD 300)
Located on Fitch Mountain is this three-story home consisting of three-bedrooms and two-bathrooms just seven minutes to Healdsburg Tipsy Timbers. This serene home is a perfect choice for a group of friends or a family as it can accommodate up to six guests. The interior includes hardwood floors throughout and outstanding decor. The garage space has been redesigned and can hosts a ton of fun games including pool/ping pong table and darts. Situated a short walk to the banks of Russian River which offers an opportunity for outdoor fun activities ranging from swimming to winery tours, hiking, biking, kayaking, and having meals from top restaurants in town.
Top guest reviews
Amenities & Room:
The bottom bedroom occupants have to go up a flight of stairs and thru the bedroom on the middle floor to use the bathroomWe loved the large kitchen and large dining space With bedrooms on each floorWe went on a hike that's accessible directly from the home with a great view of the townAll of the amenities were really nice and the kitchen was amply supplied with everything we needed to cook dinners in the eveningThe kitchen was well equipped with everything we needed and the house felt very comfortableCleanliness:
The house was very clean and well equippedthe showers were spacious (great water pressure)It was extremely hot while we were thereThe views are peaceful and brightHost:
She was super quick to respond to any questions we hadWe got all of the check-in instructions with directions well in advance as well as a whole list of recommendations for the areaand she even emailed me one morning when her gardener accidentally came on the wrong day to trim some limbsAfter booking they sent over a ton of recommendations and provided detailed instructions upon arrivalbut they only have small platesRead more reviewsLocation:
It's convenient to lots of beautiful scenery and wineriesThe house is very convenient to downtown Healdsburg and Nez had several suggestions of things to tryand it is a very peaceful house to come back to after a long day of exploring the areaWe took Uber to and from downtown Healdsburg which took only 10 minsThe location is quite unique - its only a 10 minute drive from downtown Healdsburg but feels much farther
8. Renovated luxury three-bedroom paradise (from USD 655)
This haven has three bedrooms, two and a half bathrooms and comfortably accommodates six guests. Coop is a beautifully designed vineyard home in a prime location near wineries & restaurants. Two bedrooms have king-size beds and a private bathroom with rain head showers and the third is also cozy with half bath. Highlights include a fully-equipped kitchen and gas grill. Enjoy meals on the deck and watch the sunset on the vineyards or linger in a relaxing hot tub. The Russian River also has a lot of fun activities to offer the family. You will have a great time here!
9. Exclusive home with overlooking great scenery (from USD 375)
This elegant riverside home offers three spacious bedrooms and two bathrooms. It accommodates up to eight guests thus suitable for a family or large group of travelers. Stylishly furnished, this home includes vaulted ceiling, large windows letting plenty of light into the open living room, television and stereo system, a fireplace, and a kitchen that opens on to the patio. A gas barbecue is available for grilling and patio furniture for outdoor relaxation. Located near local attractions like the beach, charming boutiques, art galleries, and antique shops, wineries, and restaurants.
Fun in Healdsburg
The variety of fun things to do in Healdsburg, California, will leave you spoilt for choice. Find your Vrbo vacation rental today and book yourself one for yourself and your loved one(s).
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