Holiday houses in Windsor

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top Guest favourite
Guesthouse in Healdsburg
4.98 out of 5 average rating, 307 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

Guest favourite
The living area showcases a tufted gray sofa adorned with vibrant decorative pillows. A round mirror reflects light from a nearby window, while a wooden table adds character. A Smart TV is mounted on the wall, and a compact desk provides a workspace.
Apartment in Junior College
4.93 out of 5 average rating, 189 reviews

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

Top Guest favourite
The exterior of a charming Victorian house is visible, featuring a welcoming front porch with a green door. Lush greenery and colorful plants frame the entrance, and a rustic wooden cart is placed nearby on a gravel pathway, enhancing the inviting outdoor space.
Home in Windsor
4.99 out of 5 average rating, 125 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.

Top Guest favourite
The inviting guest suite features a queen bed with soft linens, complemented by a cozy seating area with a light-colored sofa. Natural light flows through the plantation shutters, enhancing the neutral tones of the decor. A small table is set with a notepad and pen.
Guest suite in Windsor
4.97 out of 5 average rating, 462 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.

Top Guest favourite
The studio cottage features a balanced layout with a queen bed highlighted by wooden furnishings. A small desk and an ergonomic chair are positioned near a wall-mounted television. Natural light illuminates the space through two windows, creating a comfortable environment.
Guesthouse in Santa Rosa
4.89 out of 5 average rating, 1,191 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
The exterior of a rustic winery building is featured, characterized by its earthy tones and distinctive red door accents. Lush greenery and blooming purple flowers surround the structure, enhancing its natural setting. The building's design includes terracotta roofing and large windows that invite an abundance of natural light.
Farm stay in Healdsburg
4.97 out of 5 average rating, 644 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

Guest favourite
An open living space seamlessly connects with an outdoor deck, featuring a dining table set for several. Natural light floods the area, highlighting wooden flooring and a cozy rug. Lush greenery can be seen in the garden area beyond the deck, creating a serene atmosphere.
Home in Healdsburg
4.94 out of 5 average rating, 192 reviews

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.

Top Guest favourite
A spacious living area features a blue sofa adorned with a soft orange throw. A large area rug with intricate patterns anchors the space, while natural light floods in through large windows. A wooden coffee table rests centrally, complemented by decorative items.
Home in Windsor
4.96 out of 5 average rating, 432 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
A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.
Home in Healdsburg
5 out of 5 average rating, 209 reviews

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!

Guest favourite
The living room showcases a spacious sectional sofa adorned with decorative pillows. A wall-mounted TV is visible alongside a contemporary shelf displaying plants and decor. Natural light filters through the window treatments, highlighting the neutral tones of the furnishings.
Home in Santa Rosa
4.92 out of 5 average rating, 241 reviews

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!

Guest favourite
A cozy living area features a light-colored sofa adorned with patterned cushions. A small wooden table sits in front, with a glass of water on it. A sliding glass door opens to the private patio, providing natural light and outdoor views.
Guest suite in Santa Rosa
4.77 out of 5 average rating, 441 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

Top Guest favourite
A bright living area features a cozy twin size daybed with patterned pillows. Two upholstered chairs with a cow print design sit across from each other on a colorful area rug. Natural light streams through the windows adorned with shutters, creating a welcoming atmosphere.
Apartment in Santa Rosa
4.99 out of 5 average rating, 307 reviews

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

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
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. temp10°C10°C11°C11°C12°C13°C14°C14°C15°C13°C12°C10°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!

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Windsor