Family-friendly holiday rentals in Windsor

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Top-rated family-friendly rentals in Windsor

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Top guest favourite

Guest house in Sebastopol

4.93 out of 5 average rating, 790 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.

Top guest favourite

Guest suite in Windsor

4.97 out of 5 average rating, 450 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.

Guest favourite

Guest suite in Santa Rosa

4.85 out of 5 average rating, 247 reviews

Cozy private quiet in-law with garden entrance

Our studio has a private entrance with SELF CHECK IN. Our city permit is SVR25-056. We are close to a lovely spot to run, walk or cycle at Paulin Creek Preserve. Grocery stores (including an organic one) and a variety of restaurants, coffee shops, and retail outlets are nearby. The views from your private covered deck are serene. You’ll love our place because of the outdoors space, light, comfy bed, and quiet neighborhood. It is good for couples, solo adventurers, and business travelers.

Top guest favourite

Guest house in Santa Rosa

4.89 out of 5 average rating, 1,167 reviews

Clean Comfy Cottage Downtown

Our tree shaded studio cottage is one block from the heart of downtown. Stay just a two block walk from Russian River Brewing. This clean and quiet cottage has a full kitchen, a comfortable queen bed. I am happy to customize the space to your needs. I offer soft and firm mattresses. I use cotton blankets so that you can have any weight on your bed that you would like. You are welcome to stack seven or more blankets at a time. I will adjust my cleaning regimen to meet your preferences.

Top guest favourite

Flat in Windsor

4.97 out of 5 average rating, 109 reviews

Pool + 4 Hot Tubs! Gym, Luxury 2 bedroom villa.

Two Bedroom Twins: King in master, twins in second bedroom, queen Murphy bed in living area. Maximum occupancy 6. Full Kitchen: Unit includes refrigerator, sink, range and dishwasher. Resort has Pool, Children's Pool, Hot Tub, and much more. ❤ Free Parking. Free Internet ❤ ★ If reserving a FRIDAY OR SATURDAY there is a 2 night minimum unless request is made last minute (3 days before check in)★ ★24 hour reception★ ★Calendars updated daily★ ★Multiple Units/Room Sizes Available★

Guest favourite

Guest suite in Junior College

4.95 out of 5 average rating, 222 reviews

Cozy Private Guest Suite Centrally Located

This recently remodeled guest suite in Santa Rosa’s Junior College neighborhood offers a cozy retreat for 1-2 guests. It features a queen-size bed with a natural latex mattress, Smart TV, WiFi, mini fridge, microwave, Keurig coffee maker, and electric kettle. Relax in the shared garden courtyard with Adirondack chairs, a bistro table, and a propane grill. On-street parking is plentiful, and with a Walk Score of 85, you’re close to shops, dining, and the college.

Top guest favourite

Farm stay in Healdsburg

4.97 out of 5 average rating, 617 reviews

Gracianna Winery Vineyard Loft - Farm Stay

Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

Superhost

Flat in Windsor

4.87 out of 5 average rating, 182 reviews

Windsor 2 Bed/2 Bath Condo ~Pool~Hot Tub~Gym

***Condo: 1,023 square feet 2 bedroom/2 bath- King size bed in the master bedroom, two twin beds in the 2nd bedroom (can be put together to make a king), and one queen Murphy bed in the living room. Additional amenities include a full kitchen and dining area, gas fireplace, washer and dryer and a private terrace with gas barbecue. Maximum occupancy is six. *** twin beds in 2nd bedroom can be put together to make a king size bed. Please request in advance.

Top guest favourite

Home in Windsor

4.96 out of 5 average rating, 425 reviews

Winelight Vineyard Home With Spa

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.

Top guest favourite

Flat in Santa Rosa

4.99 out of 5 average rating, 300 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. Permit #SVR23-170

Guest favourite

Guest suite in Santa Rosa

4.91 out of 5 average rating, 312 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.

Top guest favourite

Guest suite in Santa Rosa

4.99 out of 5 average rating, 372 reviews

The Suite Life! Permit Number#SVR24-040

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