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Windsor vacation rentals

We found 1,047 vacation rentals — enter your dates for availability

Select from 30 houses, 28 condos, and other vacation rentals to find the perfect place for your stay in Windsor. Whether you’re staying in a vacation home with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. Whatever you're looking for, you'll find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Windsor

Showing deals for:Mar 27 - Apr 3

Image gallery for Private Wine Country Retreat - Modern Luxury Estate

Outdoor spa tub
10 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

Private Wine Country Retreat - Modern Luxury Estate

Healdsburg

5% off
Price is CA $1,917
CA $16,525 total
includes taxes & fees
Private Wine Country Retreat - Modern Luxury Estate

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Find out more about Windsor

Why visit Windsor

  • Charming downtown: Experience the warm hospitality of friendly locals and explore unique shops and eateries in downtown Windsor.
  • Scenic outdoor activities: Enjoy the picturesque landscapes with opportunities for hiking, biking, and relaxing by the serene river and nearby beaches.
  • Family-friendly experiences: Engage in various activities suitable for all ages, ensuring a memorable time for families visiting Windsor.
  • Romantic getaways: Discover perfect spots for couples to unwind and enjoy quality time together amidst beautiful surroundings.
  • Diverse accommodations: Choose from an array of vacation rentals, including cozy cottages and spacious homes for a comfortable stay.

Popular types of accommodation in Windsor

If you're considering a getaway to Windsor, you're in for a treat. Our vacation rentals offer a variety of popular accommodations, including houses, charming cottages, and cozy apartments. Whether you're looking to stay in a spacious Windsor house, a comfortable bedroom home, or explore options in South Windsor, we have the perfect spot for you. Enjoy your stay in Windsor with transparency and savings, ensuring a memorable experience.

  • Houses: The top choice for visitors in Windsor, offering spacious and comfortable stays ideal for families or groups.
  • Cottages: A charming option that provides a cozy and picturesque retreat, perfect for a relaxing getaway.
  • Apartments: Convenient and modern, these rentals are great for travellers seeking a home-like atmosphere.
  • Cabins: Nestled in nature, cabins offer a rustic experience for those wanting to unwind in a serene setting.
  • Villas: Luxurious and spacious, villas are perfect for those looking to indulge during their holiday.**

Top attractions near Windsor

Windsor, California, is a charming destination perfect for outdoor enthusiasts and romantic getaways. Visitors can explore picturesque sites such as piazzaSquare, the serene river, and nearby beaches. The area offers a variety of attractions that cater to those seeking cultural experiences, family-friendly activities, and beautiful scenery. Whether you're visiting with loved ones or embarking on a solo adventure, Windsor promises a memorable vacation experience.

  • Russian River: A picturesque river located 3.2km from Windsor, perfect for outdoor activities like kayaking and picnicking amidst stunning natural scenery.
  • Healdsburg Plaza: Situated 8.0km away, this vibrant square offers a cultural experience with local shops, art galleries, and restaurants, all infused with a charming city vibe.
  • Sonoma County Fairgrounds: Located 16.1km from Windsor, this family-friendly venue hosts various outdoor events and fairs, providing a fun atmosphere for all ages.

Things to do recommended for couples

Windsor offers delightful couple experiences. Visit the charming Kendall-Jackson Wine Estate and Gardens for a romantic wine tasting, or enjoy the lively atmosphere at Russian River Vineyard. For some fun, try your luck at Pee Wee Golf and Arcade, just a short drive away.

Things to do recommended for families

During your family vacation in Windsor, enjoy sweet treats at Powell's Sweet Shoppe, unwind at Spring Lake Park, just 17.7km away, or have fun ice skating at the Redwood Empire Ice Arena, located 11.3km from Windsor. It’s a perfect blend of fun and relaxation.

Things to do recommended for groups

Groups visiting Windsor can enjoy the outdoor adventure at Bohemian Grove, play a round of golf at the Healdsburg Golf Club, or experience culture and entertainment at the Raven Performing Arts Theater, all within a short distance from the town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Windsor

If you're traveling with a group, bringing your family, taking your pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Windsor with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor space for social gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Windsor with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windsor: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windsor: If you’re in search of vacation rentals offering discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Windsor

Windsor, California, offers a charming blend of outdoor adventures and picturesque scenery, perfect for a romantic getaway or a family-friendly vacation. Explore downtown Windsor, where friendly locals welcome you, and indulge in the natural landscapes that surround the area. With sunny weather and plenty of recreational activities, you'll find the ideal spot for relaxation and excursions. Don't miss the opportunity to discover nearby neighborhoods that enhance your travel experience in this delightful region.

  • Santa Rosa: Located 14.5km from Windsor, Santa Rosa invites visitors to explore its stunning outdoor landscapes and family-friendly activities. This vibrant city boasts scenic parks and a picturesque river, perfect for leisurely strolls or picnics. Enjoy a variety of recreational options, including golf courses and spa treatments, making it an ideal spot for relaxation. Notable attractions include event venues for conferences and access to nearby beaches, ensuring a well-rounded travel experience.
  • Healdsburg: Just 8.0km from Windsor, Healdsburg is a charming city known for its romantic ambiance and beautiful scenery. The town is a haven for outdoor enthusiasts, featuring lush parks and a lovely river that enhances its picturesque setting. Visitors can indulge in rejuvenating body treatments and unwind at local spas. The vibrant piazza square offers a delightful space for dining and shopping, while nearby beaches provide additional opportunities for relaxation and exploration.
  • Chalk Hill: A mere 3.2km from Windsor, Chalk Hill is a hidden gem for wine lovers and outdoor adventurers alike. This scenic area is renowned for its wineries, offering tastings and tours that highlight the best of Sonoma County's wine country. The beautiful river nearby adds to the charm, providing a perfect backdrop for a romantic day out. Whether you're looking to sip fine wines or enjoy the great outdoors, Chalk Hill offers a serene escape just a stone's throw from Windsor.

Best time to go to Windsor

If you're planning a trip to Windsor, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and October, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January48.2°F (9.0°C)Light RainMostly SunnySlightly LowSlightly Low
February49.1°F (9.5°C)Light RainMostly SunnyAverageSlightly Low
March51.1°F (10.6°C)Light RainMostly SunnyAverageSlightly Low
April55.6°F (13.1°C)No Rain (Dry)Mostly SunnyAverageAverage
May60.6°F (15.9°C)No Rain (Dry)SunnyAverageSlightly High
June67.3°F (19.6°C)No Rain (Dry)SunnySlightly HighAverage
July69.8°F (21.0°C)No Rain (Dry)SunnySlightly HighAverage
August69.4°F (20.8°C)No Rain (Dry)SunnyAverageAverage
September68.0°F (20.0°C)No Rain (Dry)SunnyAverageSlightly High
October62.1°F (16.7°C)No Rain (Dry)SunnySlightly HighSlightly High
November53.1°F (11.7°C)Light RainMostly SunnySlightly LowAverage
December47.3°F (8.5°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save some money on your upcoming journey? Being flexible with your travel dates can really help, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down your search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels. You can easily create new itineraries, pick up right where you left off, or review and organize your existing plans. Any properties you've saved or booked in the past are now accessible under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Why people love visiting friendly Windsor

The area's wineries and festivals are just a few of the reasons to vacation in Windsor. This welcoming city is known for its restaurants, bird watching and hiking. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Windsor

Are you searching for attractions to see while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Windsor has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Kendall-Jackson Winery (3.6 mi / 5.9 km)
  • Kendall-Jackson Wine Estate and Gardens (3.9 mi / 6.2 km)
  • Russian River Vineyard (6.7 mi / 10.8 km)
  • Jordan Vineyard & Winery (7.6 mi / 12.3 km)
  • Korbel Winery (8.5 mi / 13.7 km)
  • Dry Creek Vineyard (9.4 mi / 15.1 km)

Exploring the natural landscape of Windsor

Whether you're looking for fun outdoor activities or just want to take in the scenery, Windsor is a great place to spend some time outside. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Russian River (2.3 mi / 3.7 km)
  • Kendall-Jackson Wine Estate and Gardens (3.9 mi / 6.2 km)
  • Safari West (6.6 mi / 10.6 km)
  • Laguna de Santa Rosa (7.1 mi / 11.5 km)
  • Old Courthouse Square (9.2 mi / 14.9 km)
  • Luther Burbank Home and Gardens (9.5 mi / 15.3 km)

Traveling to and around Windsor

The nearest airport is in Santa Rosa, CA (STS-Sonoma County), located 2.6 mi (4.2 km) from the city center.

Frequently asked questions

What is the best area to stay in Windsor when booking a vacation rental?
When considering a vacation rental in Windsor, California, the best area to stay in would be the charming downtown district. This vibrant neighbourhood offers a delightful mix of local shops, cafes, and restaurants, making it a convenient base for exploring the area. One of the top attractions nearby is the beautiful Windsor Town Green, which hosts various community events and concerts throughout the year, providing a lovely atmosphere for visitors. Additionally, the nearby Russian River is great for those who enjoy outdoor activities such as kayaking or picnicking along the riverbanks.

Another appealing option is the area surrounding Windsor's numerous vineyards and wineries. Staying here allows you to immerse yourself in the renowned Sonoma County wine culture, with plenty of opportunities for tastings and vineyard tours. This region boasts a variety of vacation rental properties, suiting different preferences and budgets, ensuring that you can find something that suits your needs.
How much does it cost to rent a vacation home in Windsor?
Prices for vacation rentals in Windsor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windsor to more spacious homes.
Are there any discounts for Windsor vacation house rentals?
You can find great discounts on house rentals in Windsor on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Windsor?
For renting a beach house in Windsor, California, it's important to note that Windsor is not directly on the coast but is situated inland, approximately 30 minutes from the beautiful beaches of Sonoma County. For beach house rentals, travellers should consider the nearby coastal towns of Bodega Bay and Jenner, which offer stunning oceanfront properties. In Bodega Bay, visitors can find charming cottages with amenities such as expansive decks for whale watching, outdoor grills for barbecues, and easy access to nearby beaches like Doran Regional Park, where sandy shores and nature trails await.

In Jenner, properties often feature breathtaking views of the Russian River meeting the Pacific Ocean, with amenities that include hot tubs, fireplaces, and spacious living areas, great for families or romantic getaways. This area is ideal for those looking to enjoy both beach and river activities, including kayaking or simply relaxing by the shore.
What is the most popular type of vacation rental accomodation in Windsor?
In Windsor, vacation houses are the most popular type of rental accommodation, with around 25 available throughout the area. These spacious homes often feature multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens, making them ideal for families or groups looking to relax after exploring the local wineries and parks. In addition to vacation houses, there are about 24 condos, which typically offer modern amenities, open-plan living areas, and access to shared facilities like pools or fitness centres. Several apartments, villas, and mobile homes also cater to different preferences, ensuring a variety of options for travellers seeking a comfortable stay in this charming town.
Are there any family house rentals in Windsor?
In Windsor, California, there are numerous family-friendly homes available, making it an appealing destination for those travelling with children. The area features a variety of properties, many of which are located near the charming town centre and close to local parks. Families can find accommodations with spacious living rooms, fully equipped kitchens for preparing meals, and outdoor areas for relaxation or play.
Can I rent a vacation home with a pool or hot tub in Windsor?
In Windsor, California, there are many vacation homes available for rent that come with pools or hot tubs, with around 37 options to choose from. This charming town, located in Sonoma County, is surrounded by beautiful vineyards and offers a tranquil setting for a getaway.
Can I find long-stay vacation rentals in Windsor?
A long-stay vacation rental in Windsor is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Windsor?
In Windsor, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these vacation homes offer amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them suitable for families or groups.
Are there any remote work vacation rentals in Windsor?
In Windsor, California, there are numerous vacation rentals suitable for remote work, with around 56 available options. This vibrant town offers a variety of accommodations that cater to the needs of remote workers. Many properties include amenities such as reliable Wi-Fi, dedicated office spaces, and comfortable desk setups, ensuring a productive environment.

Travellers can expect to find rentals with spacious living areas, which may also feature desks and ergonomic chairs to facilitate long working hours. In addition, some properties come equipped with essentials like kitchen facilities, allowing for convenient meal preparation during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Windsor vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Windsor with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Windsor?
In Windsor, popular vacation rental amenities include fully equipped kitchens, which allow guests to prepare their own meals. Many rentals also feature pools, providing a refreshing option for relaxation, especially during warm weather. Additionally, amenities such as coffee makers, refrigerators, and microwaves are commonly available, ensuring that guests have convenient access to refreshments and quick meal options.
When is the best time to visit Windsor for a vacation rental?
The best time to visit Windsor for a vacation rental is during the vibrant month of October. This period marks the peak of the grape harvest in California's wine country, making it an ideal time for wine enthusiasts and those looking to enjoy the beautiful autumn scenery. With temperatures typically ranging in the pleasant low 20s Celsius, visitors can comfortably explore the picturesque vineyards and partake in various wine tastings and festivals.

Between August and October, Windsor buzzes with activity as tourists flock to the region for its renowned wine events, outdoor activities, and stunning landscapes. October, in particular, offers a unique blend of pleasant weather and fewer crowds, allowing for a more relaxed experience while enjoying the local wineries and the charming town vibe.

If you're seeking a more budget-friendly time to visit, November presents a quieter opportunity to explore Windsor. While the grape harvest concludes, the changing foliage and crisp air create a serene atmosphere superb for leisurely walks or cosy evenings by the fireplace in your rental.
How early should I book a Windsor vacation rental?
Book your Windsor vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Windsor home rental booking on Vrbo?
To find Windsor vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Windsor vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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