
Holiday houses in Windsor
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Top-rated holiday rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness and more.

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

1 Bedroom Garden Apmt, Smart TV/AC, 85 Walk Score
Escape to our charming 1-bedroom courtyard apartment, thoughtfully designed for a cozy and comfortable stay. The kitchenette is fully equipped with a retro-style refrigerator, countertop oven with air fry capabilities, double hot plate, electric frying pan, and a versatile marble table/island. Relax in the inviting living area with a full-size sofa, desk, and Smart TV, or step through the sliding door to enjoy your morning coffee at the bistro table overlooking the shared courtyard garden. The s

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.

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.

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.

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

Wine Country Cottage Walkable to River or Downtown
Centrally located retreat 5 blocks from downtown, Russian River and 3 blocks from at least 9 wineries. Living room fully opens to private deck w/BBQ, outdoor kitchen, dining space and fire place. Gourmet equipped kitchen with many cooking amenities to enjoy wine and a great meal in the garden patio or BBQ outside and relax. Luxury bathroom with heated towel rack, heated floor and bidet. A small cozy two bedroom with many amenities and thoughtful touches.

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.

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!

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!

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
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor

Wine Country Cottage in Santa Rosa

Sonoma Windsor Wine Country 2 bedroom Sleeps 6!

Enchanting Russian River Retreat

Lovely older home w/ private rm and bath/tub.

Sunny View Loft

Wine and Golf Paradise in Windsor, CA (#1)

Donner Dos Wine Country Retreat

The Farmhouse at Mark West, by Vinifera Homes
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $301 AUD | $298 AUD | $298 AUD | $297 AUD | $300 AUD | $330 AUD | $322 AUD | $304 AUD | $294 AUD | $324 AUD | $312 AUD | $309 AUD |
| Avg. temp | 10°C | 10°C | 11°C | 11°C | 12°C | 13°C | 14°C | 14°C | 15°C | 13°C | 12°C | 10°C |
Frequently Asked Questions
Where should I stay in Windsor?
Make yourself at home in Windsor by choosing from our most frequently booked neighborhoods. We have over 440 vacation rentals in Fulton, and over 280 vacation rentals in East Windsor.
Are there vacation rentals with a dedicated workspace in Windsor?
Yes! Work meets play with ease at over 140 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Windsor?
Four-legged friends are welcome in Windsor. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there Windsor vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 260 vacation homes with pools in Windsor, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in apartment rentals in Windsor?
Experience the best of Windsor with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do condo rentals in Windsor have a gym?
Absolutely! We offer over 120 condo rentals with a gym in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Windsor have self check-in?
Absolutely! We offer over 60 condo rentals with self check-in in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Windsor have a bbq area?
Absolutely! We offer over 60 apartment rentals with a bbq area in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Windsor have wifi?
Absolutely! We offer over 120 condo rentals with wifi in Windsor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly condo rentals in Windsor?
Windsor has more than 100 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about holiday rentals in Windsor

Total holiday rentals
Explore 340 holiday rentals in Windsor

Nightly prices starting at
Windsor holiday rentals start at $45 AUD per night before taxes and fees

Verified guest reviews
Over 8,070 verified reviews to help you choose

Family-friendly holiday rentals
250 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday rentals with a pool
260 properties feature pools

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wi-Fi availability
320 of Windsor holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Windsor rentals

4.9 Average rating
Windsor stays are highly rated by guests—averaging 4.9 out of 5!
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