Vacation Rentals & House Rentals in Healdsburg

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288 house rentals

    52

    Stunning vineyard views from the private deck at this wine-lovers house!

    Sonoma County / Healdsburg

    Healdsburg house

    3 8 min stay varies

    • 3 bedrooms
    • sleeps 8
    • min stay varies
    • Child Friendly
    • Car not necessary
    • Air conditioning

    Price per night from

    $489

    Responds fast!
    avg. 3 hours 4 minutes

    Price per night from

    $489

      10

      Dry Creek Vineyard Estate Guest Cottage

      Sonoma County / Healdsburg

      Healdsburg house

      1 2 2 nights min

      • 1 bedroom
      • sleeps 2
      • 2 nights min
      • Swimming pool
      • Pet Friendly
      • Private garden

      Price per night from

      $487

      Price per night from

      $487

      (14) Excellent 

        31

        Spectacular Two-Story Tuscan Villa Estate Home w/ Spa, Decks & Views

        Sonoma County / Healdsburg

        Healdsburg house

        4 8 min stay varies

        • 4 bedrooms
        • sleeps 8
        • min stay varies
        • Child Friendly
        • Air conditioning
        “Beautiful home!” 8 women rented this home together for a 40th birthday party. It was perfect! We were close to wine tasting and the house was private and beautiful. It was perfect for friends but not super private for couples (the walls were thin and
        …see more

        Price per night from

        $1,025

        Price per night from

        $1,025

        (22) Excellent 

          24

          Stunning Wine Country Gated Estate w/ in-ground pool & spa

          Sonoma County / Healdsburg

          Healdsburg villa

          4 10 2 nights min

          • 4 bedrooms
          • sleeps 10
          • 2 nights min
          • Swimming pool
          • Child Friendly
          • Air conditioning
          “5 stars is just not enough.” Everything about it is wonderful. Not one detail has been left off. It's comfort and luxury rolled in to one.
          …see more

          Price per night from

          $1,432

          Price per night from

          $1,432

          (4) Very Good 

            29

            Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)

            Sonoma County / Healdsburg

            Healdsburg house

            5 12 min stay varies

            • 5 bedrooms
            • sleeps 12
            • min stay varies
            • Swimming pool
            • Child Friendly
            • Pet Friendly
            “Perfect relaxing retreat with plenty of space” We stayed at this property for a girls weekend (my bachelorette trip, to be exact.) It was perfect! Exactly what we were looking for - which was plenty of space for 12 adults, a pool and a beautiful set
            …see more

            Price per night from

            $1,254

            Price per night from

            $1,254

            (5) Excellent 

              22

              Newly Renovated home w/ Spa, Gardens, & Spectacular Vineyard Views

              Sonoma County / Healdsburg

              Healdsburg house

              3 8 min stay varies

              • 3 bedrooms
              • sleeps 8
              • min stay varies
              • Child Friendly
              • Air conditioning
              • Pet Friendly
              “Terrific home base for Healdsburg and Dry Creek Valley vineyards” The home is conveniently located near downtown Healdsburg and the Dry Creek & Alexander Valley wine regions. The home is modern, spacious and comfortable. Amenities include a large kitc
              …see more

              Price per night from

              $516

              Price per night from

              $516

                15

                Healdsburg Cypress House

                Sonoma County / Healdsburg

                Healdsburg house

                3 6 4 nights min

                • 3 bedrooms
                • sleeps 6
                • 4 nights min
                • Nearest beach 40 mi
                • Child Friendly
                • Air conditioning

                Price per night from

                $796

                Price per night from

                $796

                  20

                  4BR/3BA Healdsburg Home with Gardens and Views

                  Sonoma County / Healdsburg

                  Healdsburg house

                  10 3 nights min

                  • sleeps 10
                  • 3 nights min
                  • Nearest beach 10 mi
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $974

                  Price per night from

                  $974

                    26

                    Stunning Mountain Top Estate with View Over Dry Creek Vineyards

                    Sonoma County / Healdsburg

                    Healdsburg villa

                    3 8 3 nights min

                    • 3 bedrooms
                    • sleeps 8
                    • 3 nights min
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $911

                    Responds fast!
                    avg. 37 minutes

                    Price per night from

                    $911

                    (5) Excellent 

                      25

                      Newly renovated & refurnished one-story 4br/3ba home, sleeps up to 8 guests

                      Sonoma County / Healdsburg

                      Healdsburg house

                      4 8 min stay varies

                      • 4 bedrooms
                      • sleeps 8
                      • min stay varies
                      • Child Friendly
                      • Air conditioning
                      “Fabulous Vacation Rental” This property was perfect for our wine weekend getaway. Eight of us were very comfortable in this spacious, contemporary home. The house was clean and fully stocked which made it easy and enjoyable to cook meals. It's conve
                      …see more

                      Price per night from

                      $859

                      Price per night from

                      $859

                        23

                        Healdsburg home with pool and views 10 min. to plaza

                        Sonoma County / Healdsburg

                        Healdsburg house

                        4 8 3 nights min

                        • 4 bedrooms
                        • sleeps 8
                        • 3 nights min
                        • Swimming pool
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $1,374

                        Price per night from

                        $1,374

                          25

                          River View - Riverfront Getaway in Healdsburg - Hot tub, Kayaks, River Access

                          Sonoma County / Healdsburg

                          Healdsburg house

                          3 8 min stay varies

                          • 3 bedrooms
                          • sleeps 8
                          • min stay varies
                          • Child Friendly

                          Price per night from

                          $332

                          Responds fast!
                          avg. 37 minutes

                          Price per night from

                          $332

                          (1) Excellent 

                            26

                            Beautiful mountain top wine retreat in Healdsburg!

                            Sonoma County / Healdsburg

                            Healdsburg house

                            3 6 2 nights min

                            • 3 bedrooms
                            • sleeps 6
                            • 2 nights min
                            • Beach / lakeside relaxation
                            • Child Friendly

                            Price per night from

                            $401

                            Price per night from

                            $401

                              22

                              Serene Riverfront Cottage ­ In Healdsburg, Views, Kayaks, 1.5 Mile to Downtown

                              Sonoma County / Healdsburg

                              Healdsburg house

                              2 6 min stay varies

                              • 2 bedrooms
                              • sleeps 6
                              • min stay varies
                              • Child Friendly

                              Price per night from

                              $258

                              Responds fast!
                              avg. 37 minutes

                              Price per night from

                              $258

                                35

                                Stunning 3BR Overlooking Vineyards w/ Pool, Hot Tub, Fire Pit & Guest Suite

                                Sonoma County / Healdsburg

                                Healdsburg house

                                3 8 min stay varies

                                • 3 bedrooms
                                • sleeps 8
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $1,036

                                Price per night from

                                $1,036

                                (1)  

                                  78

                                  Dog-friendly home with a deck, patios & hot tub, in the heart of wine country!

                                  Sonoma County / Healdsburg

                                  Healdsburg house

                                  2 6 min stay varies

                                  • 2 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Child Friendly
                                  • Car not necessary
                                  • Air conditioning

                                  Price per night from

                                  $202

                                  Responds fast!
                                  avg. 3 hours 4 minutes

                                  Price per night from

                                  $202

                                    25

                                    Charming 2BR by Vineyards w/ Deck, Fire Pit, Fireplace, Pool & Hot Tub

                                    Sonoma County / Healdsburg

                                    Healdsburg house

                                    2 6 min stay varies

                                    • 2 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Swimming pool
                                    • Child Friendly
                                    • Air conditioning

                                    Price per night from

                                    $919

                                    Price per night from

                                    $919

                                      14

                                      New Contemporary Wine County Home

                                      Sonoma County / Healdsburg

                                      Healdsburg house

                                      3 6 2 nights min

                                      • 3 bedrooms
                                      • sleeps 6
                                      • 2 nights min
                                      • Child Friendly
                                      • Private garden

                                      Price per night from

                                      $573

                                      Price per night from

                                      $573

                                      (5) Very Good 

                                        20

                                        Upscale, Modern four bedroom, three bath home

                                        Sonoma County / Healdsburg

                                        Healdsburg house

                                        3 8 2 nights min

                                        • 3 bedrooms
                                        • sleeps 8
                                        • 2 nights min
                                        • Swimming pool
                                        • Child Friendly
                                        • Pet Friendly
                                        “The house was very spacious and had everything we could want.” We really enjoyed our stay. The house was spotless and had everything we needed and more. The bedrooms were big and having 3 bathrooms was great. It was also a great location. Thanks so
                                        …see more

                                        Price per night from

                                        $1,203

                                        Price per night from

                                        $1,203

                                          25

                                          Charming, Two-Story, Modernized Vintage Cottage w/ beautiful river views

                                          Sonoma County / Healdsburg

                                          Healdsburg house

                                          2 6 2 nights min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 2 nights min
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $453

                                          Price per night from

                                          $453

                                            18

                                            Good view

                                            Sonoma County / Healdsburg

                                            Healdsburg house

                                            3 8 min stay varies

                                            • 3 bedrooms
                                            • sleeps 8
                                            • min stay varies
                                            • Air conditioning

                                            Price per night from

                                            $682

                                            Responds fast!
                                            avg. 1 hour 34 minutes

                                            Price per night from

                                            $682

                                            (3) Excellent 

                                              25

                                              Stunning, quiet, contemporary, single-level, eco-friendly home on 2.5 acres

                                              Sonoma County / Healdsburg

                                              Healdsburg house

                                              3 6 min stay varies

                                              • 3 bedrooms
                                              • sleeps 6
                                              • min stay varies
                                              • Swimming pool
                                              • Child Friendly
                                              “The perfect place to stay while enjoying Healdsburg'” 880 Limerick Lane was beautiful, charming, clean and perfectly appointed! The kitchen-living room space was perfect for gathering the family and enjoying shared time. The pool/hot tub and patio sp
                                              …see more

                                              Price per night from

                                              $911

                                              Price per night from

                                              $911

                                              (4) Very Good 

                                                37

                                                West Dry Creek View

                                                Sonoma County / Healdsburg

                                                Healdsburg house

                                                3 8 3 nights min

                                                • 3 bedrooms
                                                • sleeps 8
                                                • 3 nights min
                                                • Ask about children
                                                • Air conditioning
                                                • Ask about pets
                                                “Fabulous outdoor space -- great pool & spa and huge flat propert” The expansive and usable outdoor space make this property extra special. The pool is large enough for lap swimmers, the raised vegetable beds and orchard provides tasty treats, and the
                                                …see more

                                                Price per night from

                                                $1,031

                                                Price per night from

                                                $1,031

                                                  0

                                                  NEW LISTING! Wonderful estate with private pool & hot tub! Wine tasting nearby!

                                                  Sonoma County / Healdsburg

                                                  Healdsburg house

                                                  3 6 min stay varies

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Car not necessary

                                                  Price per night from

                                                  $448

                                                  Responds fast!
                                                  avg. 3 hours 4 minutes

                                                  Price per night from

                                                  $448

                                                    11

                                                    5BR/6BA 3 Cottages on 6 acres on Russian River

                                                    Sonoma County / Healdsburg

                                                    Healdsburg house

                                                    5 12 3 nights min

                                                    • 5 bedrooms
                                                    • sleeps 12
                                                    • 3 nights min
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $2,634

                                                    Price per night from

                                                    $2,634

                                                      10

                                                      The Ultimate Wine County View Estate

                                                      Sonoma County / Healdsburg

                                                      Healdsburg house

                                                      4 8 min stay varies

                                                      • 4 bedrooms
                                                      • sleeps 8
                                                      • min stay varies
                                                      • Air conditioning
                                                      • Private garden

                                                      Price per night from

                                                      $954

                                                      Price per night from

                                                      $954

                                                      (4) Excellent 

                                                        26

                                                        Lovely Healdsburg Vineyard Home - 3br/2ba (up to 8 guests, children welcome)

                                                        Sonoma County / Healdsburg

                                                        Healdsburg house

                                                        3 8 min stay varies

                                                        • 3 bedrooms
                                                        • sleeps 8
                                                        • min stay varies
                                                        • Child Friendly
                                                        • Air conditioning
                                                        • Pet Friendly
                                                        “Perfect house for a memorable bachelorette weekend” I was planning my best friend's bachelorette party and wanted everything to be perfect. When I pulled up to the house, my best friend was so excited and loved the big oak tree in the front - especial
                                                        …see more

                                                        Price per night from

                                                        $516

                                                        Price per night from

                                                        $516

                                                          40

                                                          4BR/2.5BA Estate at Pinot Hill in Healdsburg

                                                          Sonoma County / Healdsburg

                                                          Healdsburg house

                                                          4 10 3 nights min

                                                          • 4 bedrooms
                                                          • sleeps 10
                                                          • 3 nights min
                                                          • Child Friendly

                                                          Price per night from

                                                          $916

                                                          Price per night from

                                                          $916

                                                          (1) Excellent 

                                                            23

                                                            Private estate in Alexander Valley/ Views! 3 miles to town

                                                            Sonoma County / Healdsburg

                                                            Healdsburg house

                                                            3 8 2 nights min

                                                            • 3 bedrooms
                                                            • sleeps 8
                                                            • 2 nights min
                                                            • Child Friendly
                                                            “A country retreat with big views, privacy, and lots of outdoors” Kokopelli provided a wonderful spot for a family holiday. It is situated in the oak covered rolling hills overlooking the Alexander Valley with great views of the mountains and vineyar
                                                            …see more

                                                            Price per night from

                                                            $1,088

                                                            Price per night from

                                                            $1,088

                                                              24

                                                              Picturesque 1BR by Vineyards & Garden w/ Pool & Porch - Minutes to Downtown

                                                              Sonoma County / Healdsburg

                                                              Healdsburg house

                                                              1 2 min stay varies

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $362

                                                              Price per night from

                                                              $362

                                                              (7) Average 

                                                                14

                                                                Wine Country Cottage

                                                                Sonoma County / Healdsburg

                                                                Healdsburg house

                                                                2 6 3 nights min

                                                                • 2 bedrooms
                                                                • sleeps 6
                                                                • 3 nights min
                                                                • Ask about children
                                                                • Air conditioning
                                                                • Ask about pets
                                                                “Nice cottage in a cute wine country location” We loved staying here, it was comfy, cozy and walking distance to the cute little town of Healdsburg. It had all the amenities we needed and the cottage was very comfy and we had a blast hanging out in th
                                                                …see more

                                                                Price per night from

                                                                $458

                                                                Price per night from

                                                                $458

                                                                  21

                                                                  Newly renovated 3 Bedroom 2.5 Bath vineyard home with pool

                                                                  Sonoma County / Healdsburg

                                                                  Healdsburg house

                                                                  3 8 min stay varies

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $1,025

                                                                  Price per night from

                                                                  $1,025

                                                                    25

                                                                    Hilltop Vista Villa

                                                                    Sonoma County / Healdsburg

                                                                    Healdsburg villa

                                                                    2 4 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • min stay varies

                                                                    Price per night from

                                                                    $516

                                                                    Price per night from

                                                                    $516

                                                                      44

                                                                      Kenya's Kastle

                                                                      Sonoma County / Healdsburg

                                                                      Healdsburg house

                                                                      3 8 30 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 8
                                                                      • 30 nights min
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $210

                                                                      Price per night from

                                                                      $210

                                                                        15

                                                                        Enchanting Wine Country Villa

                                                                        Sonoma County / Healdsburg

                                                                        Healdsburg villa

                                                                        4 10 3 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 10
                                                                        • 3 nights min
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $1,712

                                                                        Responds fast!
                                                                        avg. 37 minutes

                                                                        Price per night from

                                                                        $1,712

                                                                          24

                                                                          Upscale Modern Vineyard Home

                                                                          Sonoma County / Healdsburg

                                                                          Healdsburg house

                                                                          2 4 3 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • 3 nights min
                                                                          • Child Friendly
                                                                          • Car not necessary
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $556

                                                                          Price per night from

                                                                          $556

                                                                            6

                                                                            Healdsburg Downtown Cottage

                                                                            Sonoma County / Healdsburg

                                                                            Healdsburg cottage

                                                                            2 4 30 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • 30 nights min
                                                                            • Nearest beach 29 mi
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $287

                                                                            Responds fast!
                                                                            avg. 3 hours 2 minutes

                                                                            Price per night from

                                                                            $287

                                                                              13

                                                                              The Residence

                                                                              Sonoma County / Healdsburg

                                                                              Healdsburg villa

                                                                              4 8 min stay varies

                                                                              • 4 bedrooms
                                                                              • sleeps 8
                                                                              • min stay varies
                                                                              • Air conditioning
                                                                              • Private garden

                                                                              Price per night from

                                                                              $2,519

                                                                              Price per night from

                                                                              $2,519

                                                                              About Healdsburg

                                                                              Located along the Russian River at the center of Sonoma County wine country, Healdsburg offers a perfect vacation paradise, especially for wine lovers and outdoor enthusiasts. Every year, visitors come here from all over the world to experience tours through the rolling hillsides covered with vineyards and olive groves. Some of the finest award winning olive oils, wines, and champagnes in the world are produced right here. The mountains lie within easy reach of downtown Healdsburg, offering endless outdoor activities against a backdrop of rugged natural beauty. Stay in your own private vacation rental and enjoy a cup of coffee on your deck as the sun rises. Head into town for shopping, art galleries, craft studios, and seasonal festivals. When you're ready to explore the wilderness, there are miles of scenic trails and picnic areas here offering beautiful overlooks and wildlife spotting opportunities. At night, come home to your vacation rental in Healdsburg. Pool and luxury gourmet kitchens are features that many rentals offer, which can make your private condo or vacation home a great place for relaxing in style or hosting dinner for your family and friends.

                                                                              Here are a few additional suggestions for your trip:

                                                                              • Tour wine country: A vineyard tour is an indispensible part of the Healdsburg Experience.
                                                                              • Go biking: Explore the steep back country trails by bicycle or rent a bike and peddle around town and have a freewheeling afternoon on a bicycle wine tour.
                                                                              • Take a balloon ride: Experience the majestic beauty of Sonoma from the sky. Take a ride in a colorful balloon at sunrise and follow it up with a romantic champagne brunch.
                                                                              • Go boating and fishing: Head out onto Healdsburg's tranquil lakes and waterways for some of the best fly fishing opportunities in the state.
                                                                              • Spend an afternoon in the spa: Healdsburg spa venues are truly world class. After a few days of mountain biking and rock climbing, indulge in an afternoon of serious pampering.
                                                                              • Go bird watching and wildlife spotting: The Healdsburg area is home to some of California's most elusive bird and wildlife species. Come here to see eagles, hawks, otters, foxes, and black bears.

                                                                              Sonoma country is becoming increasingly popular for weekend getaways, family reunions, and Healdsburg wedding locations. Bring your friends and family, rent a luxury vacation home or seasonal condo, and let the vacation memories begin.