Holiday houses in Windsor

4.98 out of 5 average rating, 291 reviews

Guesthouse in Healdsburg

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

4.94 out of 5 average rating, 16 reviews

Apartment in Windsor

Sonoma Windsor Wine Country 2 BD

Your request will be declined if you request to book BEFORE clicking "message host" to confirm that this unit is available. Some airbnbs are "instant book" but this one is not. This means your booking is not confirmed until we go through a quick checklist to make sure it's a great fit for you! This is a professionally managed resort (Wyndham) featuring 2 bd and 2 bathrooms with either 4 or 5 beds. Lots of cool amenities including BBQ grills, pools, hot tubs, gym, game room and a spa on site!

5 out of 5 average rating, 34 reviews

Home in Healdsburg

Vineyard Oasis: Luxury Home in the Heart of Sonoma

Wake up to vineyard views and the serenity of Sonoma’s wine country. Nestled amidst the serene vineyards of the Chalk Hill AVA, our recently remodeled house offers breathtaking views of the Sonoma Valley. Just minutes from world-renowned wineries like Roth and Chalk Hill, and a short drive from downtown Healdsburg and Windsor, this is the perfect retreat for those looking to explore the best of wine country or simply unwind in a peaceful, scenic setting. Exclusive Perk: 2-for-1 Wine Tasting!

4.99 out of 5 average rating, 117 reviews

Home in Windsor

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.

4.97 out of 5 average rating, 426 reviews

Guest suite 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.

4.73 out of 5 average rating, 11 reviews

Guest suite in Windsor

Private Wine Country Studio ~ Near Town & Trails

Serene wine country studio ~ your home away from home w/ kitchenette, washer/drier, gigabyte internet, Big Screen TV & tons of amenities! Peaceful covered private porch features a teak patio set where you can sip a glass of wine & read or dine al fresco! Nearby you’ll find hot air balloons, wine tasting, restaurants galore, boutique shopping, river adventures, botanical gardens & farmers markets~create & celebrate your Relaxing Wine Country experience! Please inquire about weekly discounts!

4.97 out of 5 average rating, 105 reviews

Apartment in Windsor

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★

4.96 out of 5 average rating, 118 reviews

Guesthouse in Healdsburg

Mediterranean Getaway with breakfast Healdsburg

An attractive, ultra-romantic, almost-a-cottage Bed&Breakfast is waiting for you in our restored 1930s-era home in a peaceful corner of northern Sonoma County. Ours is a quiet rural road nestled in beautiful oaks, redwoods, California bay, and buckeye trees near the bottom of Fitch Mountain, some 100’ above the Russian Rive. Fitch Mountain is known for its interesting local history, eclectic building styles, beautiful views, secluded neighborhoods, and friendly spirit.

4.88 out of 5 average rating, 171 reviews

Apartment in Windsor

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.

4.96 out of 5 average rating, 418 reviews

Home in Windsor

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.

4.92 out of 5 average rating, 229 reviews

Home in Santa Rosa

The Explorer’s Wine Country Getaway

Discover the perfect mix of ease and comfort in this charming one-bedroom bungalow, nestled in the heart of wine country. Perfect for a relaxed escape, this cozy retreat features a queen-sized bedroom, a bathroom, and a full-size pullout sofa in the living room. Every detail is designed with your comfort in mind, ensuring a stay that’s both delightful and memorable. Experience the magic of wine country living and make your getaway one to remember!

4.97 out of 5 average rating, 589 reviews

Farm stay in Healdsburg

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. 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

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Popular amenities for Windsor holiday rentals

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Other great holiday rentals in Windsor

4.69 out of 5 average rating, 127 reviews

Beautiful En-suite bedroom with balcony -room3

FrancescaRating, 5 stars1 month ago

Perfect for a short trip. If you park on the street it is a little much going up and down the steep driveway. Quiet and nice neighborhood.

5 out of 5 average rating, 16 reviews

Private room in Windsor

Wine Country Retreat 1 bedroom/hot tub

HeidiRating, 5 stars1 month ago

Michelle had great hospitality throughout my stay. Really liked the backyard (fountain, patio) & hot tub so peaceful place to relax. Very close to downtown Windsor so easy to go back & forth.

Private room in Guerneville

4.95 out of 5 average rating, 238 reviews

Sweetwater Cottage

JudyRating, 5 stars2 weeks ago

Very clean welcoming cottage. Quiet beautiful surroundings. Brendan checked to make sure I was comfortable and had filtered water and coffee.

Private room in Rohnert Park

4.78 out of 5 average rating, 162 reviews

Quiet Small Bedroom w/ Shared Bath Kitchen+TV

RondaRating, 5 stars2 weeks ago

I had a very pleasant stay and would definitely come back in the future. Thanks!

4.87 out of 5 average rating, 357 reviews

Garden View Queen Suite & Separate Entrance

BruceRating, 5 stars1 week ago

Just as advertised - small but very comfortable. Enjoyed my stay.

4.95 out of 5 average rating, 140 reviews

Willowside House

MarthaRating, 5 stars3 weeks ago

Mary’s place was very calm and beautiful. It is very much worth the pay. Mary was very nice and was flexible with checking in! The stay there was over a week and she offered to wash the sheets and offered extra towels at no cost. The dogs are so cute and friendly. I really recommend!

4.84 out of 5 average rating, 433 reviews

Small Sunny Room in Historic McDonald Neighborhood

MashaadRating, 5 stars1 week ago

Very nice place for a night or two. Place was clean and in a great location. If I’m in Santa Rosa again I was consider coming back. Great overall.