Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

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Guest favourite

Guesthouse in Sebastopol

4.93 out of 5 average rating, 678 reviews

Sun Drenched Flat

Put up the burnt-orange parasol and settle down with book on the patio while the barbecue heats up. Sitting above a garage in a serene, walkable neighborhood, this sunlit retreat's beachy cream painted paneling gives it a chilled, refined vibe. Check out all that Sebastopol has to offer at: visitsebastopolnow.come This second story house is a very desirable space, located close to town, still being set on a very beautiful street in an friendly established older neighborhood. It is nestled between other structures on the property. One being a "Tiny House" that is right next door, my home sits behind the flat. The house has a full kitchen with all the utensils and necessary cooking items, pots pans etc. Large toaster oven that will even fit your frozen pizza. There is a space in front with some Adirondack chairs and BBQ if you want to relax outside. The house has its own separate entrance off the driveway. My house is in back of the flat, I may or may not see you, but I am available for any questions at any time. You will more than likely be greeted by our white cat with orange tips (named White Boy). If he gets a chance, Charlie our very exuberant Golden Doodle will give you a warm excited welcome. Located just 1 mile from the heart of the sweet town of Sebastopol, this area is a handy stepping off point to explore nearby wineries, scenic beaches, and shopping and restaurants at redwoods. A very nice mile walk to town or a five minute drive. There is a flight of stairs that you climb to get to the Flat space, it does not have wheelchair access. There are cats on the property, but they do not go inside the flat. Our Goldendoodle is extremely friendly. The leather couch folds flat into a double bed for accommodating two more guests. Access to the bathroom is through the bedroom however. There is no dedicated parking, however the street parking directly across from the flat, just up from, but not in front of the three mailboxes is usually always open.

2–9 Mar

$269 NZD per night

Guest favourite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 249 reviews

Alexander Valley: Wine Lover and Cycling Paradise

The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N

7–14 Oct

$371 NZD per night

Guest favourite

Home in Windsor

5.0 out of 5 average rating, 99 reviews

Large Home w/ HotTub 10 min to Downtown Healdsburg

Wine Country Living at its finest. Conveniently located just 10 minutes to Downtown Healdsburg, this spacious, elegant home features 4 bedrooms, 2.5 bathrooms and an open floor plan perfect for spending time with friends and family. Relax in the hot tub or around the fire pit in the backyard, play a game of ping pong or pool in the garage, or cozy up by the fireplace in the living room. This home is perfect for your Wine Country get-a-way. Only 1.6miles to the world famous Russian River Brewery!

15–22 Jul

$1,467 NZD per night

Guest favourite

Guest suite in Windsor

4.98 out of 5 average rating, 357 reviews

Private Entrance Suite in Heart of Wine Country

Situated in an upscale neighborhood, this exquisite guest suite boasts a private entrance on a safe, quiet cul-de-sac in the heart of the wine country. The en-suite is perfect for a romantic getaway, comfortable for an infant or small child, and ideal for the business traveler. We are 5 miles from Healdsburg and 3 from the Sonoma Co. Airport. Three parks within 4 miles encompass over 20 miles of hiking/biking. The Russian River, Redwoods, and Sonoma Coast are only a short, panoramic drive away.

24–31 Jul

$237 NZD per night

Guest favourite

Home in Windsor

4.99 out of 5 average rating, 101 reviews

Gorgeous Victorian in the HEART of Windsor

Gorgeous renovated Queen Anne Victorian located in the heart of Windsor, CA combines quality finishes, modern convenience & vintage details. With a stylish kitchen, high ceilings, 3 beds/2 baths on a single level, HVAC & a huge lot with a Bocce Court. Walking distance to the Town Green, restaurants, wine tasting rooms and shopping. Just 3.5 miles from the Sonoma County Airport (STS), 5 miles to downtown Healdsburg, in the heart of the Russian River Valley & just 57 miles from the Golden Gate.

26 Jun – 3 Jul

$894 NZD per night

Guest favourite

Home in Windsor

4.96 out of 5 average rating, 378 reviews

Winelight Vineyard Home With Spa

Available for minimum 3 day rental. Gated driveway, private, scenic, safe, secure, and impeccably clean. Unwind, prepare dinner on granite counter tops in this newly remodeled well-stocked gourmet kitchen. Enjoy plush amenities, fine decor, hot tub, romantic fireplace, French doors leading to outdoor decks, secluded rural vibe, reliably fast internet. Close to Sonoma County's best wineries, breweries and restaurants. There is a guest laundry, designer carport, and ample parking for guests.

26 Jun – 3 Jul

$424 NZD per night

Guest favourite

Guest suite in Santa Rosa

4.91 out of 5 average rating, 248 reviews

Peaceful Wine Country Retreat / PRIVATE ENTRANCE

Tax ID 2726N GUEST SUITE/PRIVATE ENTRANCE with Sitting Room, Large Private Bedroom & Bath. Includes a King size bed, Cable TV, Wi-Fi and Breakfast. Enjoy the beautiful view of the garden and rolling hills of Sonoma Valley’s Wine Country while relaxing in the fully stocked sitting room sipping on a glass of wine, tea, or coffee. In the evening, unwind on the patio that is just outside of the sitting room while sitting under the stars and majestic trees.

9–16 Dec

$245 NZD per night

Guest favourite

Guest suite in Santa Rosa

4.99 out of 5 average rating, 325 reviews

The Suite Life! Permit Number#SVR22-078

Our private Airbnb is an extremely comfortable guest suite of over 700 square feet with air conditioning and a gas fireplace. It's beautifully decorated with a large sofa and dining area. You'll have complete privacy with your own entrance and parking space plus free WiFi. Located in a beautiful area. World class wineries, and parks are minutes away. Please feel free to message Janette with any questions about the suite! Permit Number#SVR22-078

26 Jun – 3 Jul

$242 NZD per night

Superhost

Home in Healdsburg

4.81 out of 5 average rating, 424 reviews

C - Wineries/breweries seconds away

Great location for a wine country getaway! Please use the Airbnb app for self check-in instructions! The owner is severely allergic to animals, so please do not request or bring any animal with you. We have an automated backup generator for loss of power issues! Full kitchen, Outdoor patio, BBQ, Fire pit (propane tank included but not fuel), Two bikes included in stay. California King Tempurpedic bed. Laundry room, Fully renovated bathroom.

11–18 Dec

$300 NZD per night

Superhost

Guest suite in Santa Rosa

4.78 out of 5 average rating, 343 reviews

Dedicated Patio, Roku & Self Check-In

Premium guest suite with private entrance, separate living room and dedicated outdoor patio area. Complete with complimentary popcorn, coffee, tea and water for your enjoyment. Located 2.4 miles to Down Town Santa Rosa & Russian River Brewing Company, half mile to groceries & restaurants, 7.4 miles to Sonoma County Airport and 2-5 miles to all major hospitals. Best for 2 guests due to size. Longer stays discounted. Permit Number: SVR21-197

3–10 Sep

$208 NZD per night

Guest favourite

Apartment in Santa Rosa

4.99 out of 5 average rating, 254 reviews

Robin's Nest

Our home is a 10 minute drive to downtown Santa Rosa, where you will find Russian River Brewing Company, 45 minute drive to the coast, and a little over an hour to San Francisco. The apartment is above our 2 car garage. It's a quiet 1 bedroom, 1 bath, living room, full kitchen and dining area. A twin size daybed is in the living room. Local grocery stores are within a mile, and close to Sonoma County wineries, breweries and hiking trails.

17–24 Jan

$208 NZD per night

Guest favourite

Home in Windsor

4.95 out of 5 average rating, 136 reviews

Home near golf course w/Hot tub in Windsor

This gorgeous home is located just minutes from Russian River Brewery, the Santa Rosa airport and Dry Creek valley. It features 3 bedrooms and 2.5 bath, a hot tub, fire pit and large kitchen for you and your guests to enjoy! It also has a WFH space so you can make it a longer stay. The park in walking distance makes it perfect for the whole family to be entertained.

20–27 Sep

$704 NZD per night