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339 Houses

    22

    Worldmark Windsor Condo 1BD

    Sonoma County / Windsor

    Windsor condo

    1 4 2 nights min

    • 1 bedroom
    • sleeps 4
    • 2 nights min
    • Swimming pool
    • Child Friendly

    Price per night from

    $134

    Price per night from

    $134

      30

      Windsor, CA: Sonoma 3 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!

      Sonoma County / Windsor

      Windsor house

      3 8 min stay varies

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

      Price per night from

      $264

      Price per night from

      $264

      (6) Excellent 

        21

        Windsor, CA Cottage in Sonoma's Wine Country

        Sonoma County / Windsor

        Windsor cottage

        2 4 2 nights min

        • 2 bedrooms
        • sleeps 4
        • 2 nights min
        • Nearest beach 35 mi
        • Child Friendly
        • Car not necessary
        “Exactly what we were looking for!” My fiancee and I rented the Carriage House with another couple on Labor Day weekend. This space was great for that circumstance and would also be great for a family. First of all, the location of the Carriage House

        Price per night from

        $344

        Price per night from

        $344

          14

          WorldMark Windsor Condo 2BD

          Sonoma County / Windsor

          Windsor condo

          2 6 2 nights min

          • 2 bedrooms
          • sleeps 6
          • 2 nights min
          • Swimming pool
          • Child Friendly

          Price per night from

          $158

          Price per night from

          $158

          (1) Excellent 

            26

            Sonoma Wine Country Suite

            Sonoma County / Windsor

            Windsor house

            2 4 2 nights min

            • 2 bedrooms
            • sleeps 4
            • 2 nights min
            • Child Friendly

            Price per night from

            $182

            Price per night from

            $182

              22

              Windsor, CA: Sonoma 2 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!

              Sonoma County / Windsor

              Windsor house

              2 6 min stay varies

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

              Price per night from

              $172

              Price per night from

              $172

              (3) Average 

                11

                Wine Country Townhouse

                Sonoma County / Windsor

                Windsor house

                3 6 7 nights min

                • 3 bedrooms
                • sleeps 6
                • 7 nights min
                • Ask about children
                • Air conditioning
                • Ask about pets

                Price per night from

                $393

                Price per night from

                $393

                  4

                  Worldmark Windsor Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

                  Sonoma County / Windsor

                  Windsor condo

                  3 8 3 nights min

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

                  Price per night from

                  $457

                  Price per night from

                  $457

                    4

                    Superbowl 50; February 3-10

                    Sonoma County / Windsor

                    Windsor condo

                    2 6 7 nights min

                    • 2 bedrooms
                    • sleeps 6
                    • 7 nights min
                    • Child Friendly

                    Price per night from

                    $571

                    Price per night from

                    $571

                      4

                      Worldmark Windsor #2 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

                      Sonoma County / Windsor

                      Windsor condo

                      3 8 3 nights min

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

                      Price per night from

                      $320

                      Price per night from

                      $320

                        27

                        Windsor, CA: Sonoma 1 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!

                        Sonoma County / Windsor

                        Windsor house

                        1 4 min stay varies

                        • 1 bedroom
                        • sleeps 4
                        • min stay varies
                        • Child Friendly

                        Price per night from

                        $144

                        Price per night from

                        $144

                          4

                          Worldmark Windsor # 9 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

                          Sonoma County / Windsor

                          Windsor condo

                          3 6 3 nights min

                          • 3 bedrooms
                          • sleeps 6
                          • 3 nights min
                          • Swimming pool
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $458

                          Price per night from

                          $458

                            4

                            Worldmark Windsor # 8 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

                            Sonoma County / Windsor

                            Windsor condo

                            3 6 3 nights min

                            • 3 bedrooms
                            • sleeps 6
                            • 3 nights min
                            • Swimming pool
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $456

                            Price per night from

                            $456

                              4

                              Worldmark Windsor #3 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

                              Sonoma County / Windsor

                              Windsor condo

                              3 8 3 nights min

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

                              Price per night from

                              $457

                              Price per night from

                              $457

                                4

                                Worldmark Windsor #5Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

                                Sonoma County / Windsor

                                Windsor condo

                                3 6 3 nights min

                                • 3 bedrooms
                                • sleeps 6
                                • 3 nights min
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $457

                                Price per night from

                                $457

                                  41

                                  Fabulous Wine Country Escape

                                  Sonoma County / Windsor

                                  Windsor house

                                  2 6 2 nights min

                                  • 2 bedrooms
                                  • sleeps 6
                                  • 2 nights min

                                  Price per night from

                                  $400

                                  Price per night from

                                  $400

                                    4

                                    Worldmark Windsor #4 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

                                    Sonoma County / Windsor

                                    Windsor condo

                                    3 8 3 nights min

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

                                    Price per night from

                                    $457

                                    Price per night from

                                    $457

                                      4

                                      Worldmark Windsor #10 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

                                      Sonoma County / Windsor

                                      Windsor condo

                                      3 6 3 nights min

                                      • 3 bedrooms
                                      • sleeps 6
                                      • 3 nights min
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $458

                                      Price per night from

                                      $458

                                        4

                                        Worldmark Windsor #6 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

                                        Sonoma County / Windsor

                                        Windsor condo

                                        3 8 3 nights min

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

                                        Price per night from

                                        $457

                                        Price per night from

                                        $457

                                        (2) Excellent 

                                          17

                                          Close to Healdsburg Plaza with Vineyard Views!

                                          Sonoma County / Windsor

                                          Windsor house

                                          3 8 2 nights min

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

                                          Price per night from

                                          $401

                                          Price per night from

                                          $401

                                            4

                                            Worldmark Windsor # 7 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

                                            Sonoma County / Windsor

                                            Windsor condo

                                            3 6 3 nights min

                                            • 3 bedrooms
                                            • sleeps 6
                                            • 3 nights min
                                            • Swimming pool
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $457

                                            Price per night from

                                            $457

                                              7

                                              Wine Country Condo #8121

                                              Sonoma County / Windsor

                                              Windsor condo

                                              3 6 30 nights min

                                              • 3 bedrooms
                                              • sleeps 6
                                              • 30 nights min
                                              • Child Friendly
                                              • Car not necessary
                                              • Air conditioning

                                              Price per night from

                                              $530

                                              Price per night from

                                              $530

                                              Great rentals within 20 miles that match your search

                                              Distance approx 9.1 km from Windsor

                                                30

                                                Downtown, 3 bdrms close to Pliny and Great food

                                                Sonoma County / Santa Rosa

                                                Santa Rosa b and b

                                                3 6 2 nights min

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

                                                Price per night from

                                                $670

                                                Responds fast!
                                                avg. 3 hours 22 minutes

                                                Price per night from

                                                $670

                                                Distance approx 5.26 km from Windsor

                                                (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

                                                  Price per night from

                                                  $455

                                                  Price per night from

                                                  $455

                                                  Distance approx 14.37 km from Windsor

                                                    25

                                                    Rustic Home in the Redwoods w/ Hot Tub!

                                                    Sonoma County / Cazadero

                                                    Cazadero house

                                                    2 4 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • min stay varies
                                                    • Child Friendly

                                                    Price per night from

                                                    $211

                                                    Responds fast!
                                                    avg. 24 minutes

                                                    Price per night from

                                                    $211

                                                    Distance approx 11.56 km from Windsor

                                                    (15) Very Good 

                                                      22

                                                      TIRNANOG: Riverfront | Fireplace | Hot Tub

                                                      Sonoma County / Monte Rio

                                                      Monte Rio house

                                                      4 10 min stay varies

                                                      • 4 bedrooms
                                                      • sleeps 10
                                                      • min stay varies
                                                      • Child Friendly
                                                      • Pet Friendly
                                                      • Private garden
                                                      “Tir Na Nog” We are six 75 year old ladies that met in grammar school and junior high. We loved hanging out in the kitchen at the wonderful nook with built in table and seats. For the four who slept upstairs getting up and down wasn't easy since the st

                                                      Price per night from

                                                      $455

                                                      Price per night from

                                                      $455

                                                      Distance approx 11.4 km from Windsor

                                                        27

                                                        Sydney's River Retreat-Handsome & Unique with Hot Tub, Forest Views, Large Deck

                                                        Sonoma County / Guerneville

                                                        Guerneville house

                                                        2 4 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Child Friendly

                                                        Price per night from

                                                        $245

                                                        Price per night from

                                                        $245

                                                        Distance approx 10.07 km from Windsor

                                                        (20) Excellent 

                                                          31

                                                          EXECUTIVE WINE COUNTRY HOME HEART OF SONOMA VALLEY

                                                          Sonoma County / Santa Rosa

                                                          Santa Rosa house

                                                          4 8 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 8
                                                          • min stay varies
                                                          • Nearest beach 61 mi
                                                          • Child Friendly
                                                          • Air conditioning
                                                          “A great place to stay in Santa Rosa!” Our weekend in Santa Rosa was a restful and relaxing experience, thanks to the extreme comforts and amenities of this beautiful home. The house Manager, Kimberly, was very friendly and greeted us promptly upon our

                                                          Price per night from

                                                          $599

                                                          Price per night from

                                                          $599

                                                          Distance approx 12.17 km from Windsor

                                                            8

                                                            The Old Cazadero Cabin

                                                            Sonoma County / Guerneville

                                                            Guerneville log cabin

                                                            1 4 2 nights min

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • 2 nights min
                                                            • Private garden

                                                            Price per night from

                                                            $188

                                                            Price per night from

                                                            $188

                                                            Distance approx 5.16 km from Windsor

                                                            (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

                                                              $399

                                                              Price per night from

                                                              $399

                                                              Distance approx 4.37 km from Windsor

                                                                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

                                                                $2,622

                                                                Price per night from

                                                                $2,622

                                                                Distance approx 16.58 km from Windsor

                                                                  9

                                                                  Bella Luna Suite at Casa Bella

                                                                  Sonoma County / Kenwood

                                                                  Kenwood cottage

                                                                  2 6 1 night min

                                                                  • 2 bedrooms
                                                                  • sleeps 6
                                                                  • 1 night min
                                                                  • Child Friendly
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $342

                                                                  Price per night from

                                                                  $342

                                                                  Distance approx 5.2 km from Windsor

                                                                    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

                                                                    $285

                                                                    Responds fast!
                                                                    avg. 3 hours 2 minutes

                                                                    Price per night from

                                                                    $285

                                                                    Distance approx 11.66 km from Windsor

                                                                      18

                                                                      Wine Country Ranchette

                                                                      Sonoma County / Santa Rosa

                                                                      Santa Rosa house

                                                                      3 6 3 nights min

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

                                                                      Price per night from

                                                                      $627

                                                                      Price per night from

                                                                      $627

                                                                      Distance approx 11.72 km from Windsor

                                                                        11

                                                                        Sanctuaire - Hot Tub, Sauna, Mini Oasis in the Russian River Area

                                                                        Sonoma County / Monte Rio

                                                                        Monte Rio house

                                                                        2 6 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Beach / lakeside relaxation
                                                                        • Child Friendly
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $240

                                                                        Price per night from

                                                                        $240

                                                                        Distance approx 8.95 km from Windsor

                                                                        (1) Excellent 

                                                                          17

                                                                          Secluded Wine Country Home - 2 acre Orchard Estate

                                                                          Sonoma County / Sebastopol

                                                                          Sebastopol house

                                                                          3 8 3 nights min

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

                                                                          Price per night from

                                                                          $443

                                                                          Price per night from

                                                                          $443

                                                                          Distance approx 5.64 km from Windsor

                                                                            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

                                                                            $1,368

                                                                            Price per night from

                                                                            $1,368

                                                                            Distance approx 18.94 km from Windsor

                                                                            (1) Excellent 

                                                                              9

                                                                              Recently Remodeled1 Bedroom Apartment near Downto

                                                                              Napa Valley / St. Helena

                                                                              St. Helena apartment

                                                                              1 4 30 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • 30 nights min
                                                                              • Nearest beach 97 mi
                                                                              • Air conditioning
                                                                              • Private garden

                                                                              Price per night from

                                                                              $124

                                                                              Price per night from

                                                                              $124

                                                                              About Windsor

                                                                              Situated within Sonoma County on California's North Coast, Windsor is a historic town dating back to the 1870s and part of the state's renowned wine country region. Today, people come from all over the globe to experience the area's exquisite natural beauty, culinary delights, outdoor activities, and of course, the unique and award-winning vineyards nearby. There are plenty of casual and fine dining restaurants to be discovered, as well as various cultural activities to enjoy downtown and within the city's parks and playgrounds. Shopping excursions for antiques, clothing, jewelry, and crafts are easy to find. Visitors will also encounter a cornucopia of fruits, vegetables, and homegrown goodies at the Windsor Farmers Market, which runs all year long.

                                                                              Here are some of the town highlights you'll want to take include in your itinerary:

                                                                              • Old Downtown Windsor: This historic hub of the city is full of shops, restaurants, and cafes.
                                                                              • Windsor Town Green: As the central spot for fun family activities, this space features plenty of room for play, picnics, outdoor concerts and more.
                                                                              • Russian Hill Estate Vineyards and/or Martinelli Vineyards: These two wineries offer tastings and tours in beautiful countryside surroundings.
                                                                              • Ballooning: A hot-air balloon experience offers truly breathtaking sights of Sonoma County Wine Country.
                                                                              • The Windsor Golf Club: This former PGA tournament stop provides a challenging course in a picturesque setting.
                                                                              • Powell's Sweet Shoppe: As an old-fashioned candy store, this is the sweet spot for adults and kids alike.

                                                                              After a long day of exploring all that Windsor has to offer, you can settle into your vacation rental, whether it be an apartment or condo downtown or a villa with spectacular vineyard views.

                                                                              Temperatures are mild year-round, but harvest time, around September and October, is the ideal season to see all the sights. There are also several annual events that are attractive to travelers including Taste Alexander Valley in May, a food and wine event, and Summer Nights on the Green, movie showings under the stars during June, July, and August.

                                                                              To continue your journey in the wine country, you can visit additional nearby attractions in Santa Rosa and Sonoma. If you are craving some big city adventure, San Francisco, is located about an hour south of Windsor.