Family-friendly vacation rentals in Windsor

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.

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.

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.

Hilltop Haven 🌅 view & hot tub

Relax with the whole family at this peaceful place to stay on a quiet hilltop. This is a quaint 2 bedroom, 1 bath with a queen bed in one bedroom and bunk (twin over full) in the second bedroom. Relax in the hot tub or in the hammock on the backyard deck with a peaceful nature view or hang inside the cozy abode and make use of the fully-stocked kitchen. we have a limit of 4 overnight guests and 2 vehicles per Sonoma County permit rules. For more pictures on IG @hilltop_haven_vacation

Wikiup lookout retreat

We self-developed our rural property as a secluded retreat with dog-friendly gardens. To share our creation with you, we designed a private 2nd-floor guest suite (ok to bring your good dogs). Your suite includes secure parking, private entrance, deck, kitchen, dining, living, 3 beds (queen, double, twin), one bath & a fenced back yard. We are on a country road near Healdsburg, Windsor, Russian River, Sebastopol, Santa Rosa, Calistoga, Sonoma & Napa valleys, wineries & beaches.

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.

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

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.

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.

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

Robin's Nest

Your second home is above our 2-car garage, a 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, a 10-minute drive to downtown Santa Rosa, 45-minute drive to the coast and little over an hour to San Francisco. We are centrally located to explore Sonoma and Napa County wineries, breweries and hiking trails. Permit #SVR23-170

Wine Country guest house

This large private studio apartment is modern and cozy. You are next to beautiful country side while you are in the city. There is a large patio for you to relax and enjoy the beautiful wine country view. You can drive or ride your bike to Sonoma Wine Country at HWY 12 or to Russian River Brewery. The Listing excludes Tax. The unit has short term permit form Santa Rosa SVR24-056.