Photo by Jennifer Hill

Windsor holiday lettings

We found 1,073 holiday rentals — enter your dates for availability

Select from 34 houses, 33 flats and other holiday rentals to find the perfect place for your stay in Windsor. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Windsor

Showing deals for:19 Dec - 26 Dec

Image gallery for Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Pool
10 out of 10, Exceptional, (63 reviews)
Exceptional
(63 reviews)

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Healdsburg, CA

12% off
Price is £10,841
for 7 nights, 1 home
£1,549 per night
includes taxes & fees
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

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    Enjoy full kitchens, pools, gardens and more

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Find out more about Windsor

Find out more about Windsor

Why people love visiting friendly Windsor

The area's wineries and festivals are just some of the reasons to come on holiday to Windsor. This welcoming city is known for its restaurants, bird watching and hiking. With a holiday 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

Do you want to discover things to do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Windsor a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Kendall-Jackson Wine Estate and Gardens (3.9 mi / 6.2 km)
  • Russian River Vineyard (6.7 mi / 10.8 km)
  • Korbel Winery (8.5 mi / 13.7 km)
  • SingleThread Farm at Dry Creek (8.7 mi / 14.1 km)
  • Dry Creek Vineyard (9.4 mi / 15.1 km)
  • Francis Ford Coppola Winery (10 mi / 16 km)

Exploring the natural landscape of Windsor

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Windsor is a great place to spend some time outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Travelling 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 centre.

Frequently asked questions

What is the best area to stay in Windsor when booking a holiday rental?
When planning a holiday rental in Windsor, California, one of the most appealing areas to consider is the Windsor Town Green. This vibrant neighbourhood is at the heart of the community and offers a delightful atmosphere with a range of amenities, including shops, cafes, and restaurants. The Town Green is particularly attractive due to its picturesque setting, featuring green spaces and a charming gazebo, making it a lovely spot for leisurely strolls or picnics.

Additionally, the Windsor Riverwalk is nearby and provides a scenic path along the Russian River, superb for walking, biking, or simply enjoying the natural surroundings. The Riverwalk connects to several parks, enhancing the outdoor experience and providing opportunities for recreation.

Another great option is the Piner-Olivet area, which is slightly more residential but still offers easy access to both the beautiful vineyards of Sonoma County and the vibrant downtown area. This neighbourhood is ideal for those who wish to explore wine country while enjoying a tranquil retreat. The proximity to attractions such as the Sonoma County Regional Parks allows visitors to partake in various outdoor activities, such as hiking and wine tasting.
How much does it cost to rent a holiday home in Windsor?
Prices for holiday 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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Windsor holiday 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 situated inland and does not directly offer beach access. However, nearby coastal towns such as Santa Rosa, Sebastopol, and Bodega Bay are within a reasonable driving distance and provide excellent beach rental options.

In Bodega Bay, travellers can find lovely beachfront properties that boast stunning views of the Pacific Ocean. Many of these rentals come equipped with amenities such as expansive decks for outdoor dining, fireplaces for cosy evenings, and fully equipped kitchens ideal for preparing fresh local seafood. The area is also close to Bodega Head, which is great for hiking and enjoying picturesque coastal scenery.

Sebastopol, located slightly further inland, offers a charming mix of rural and coastal vibes, with access to nearby beaches. Rentals here often feature rustic decor and amenities like gardens, patios, and hot tubs, allowing guests to experience a serene getaway while still being a short drive from the coast.

Santa Rosa, while more urban, provides a gateway to the beautiful Sonoma County coastline. Here, visitors can find holiday rentals that include modern amenities, such as Wi-Fi, air conditioning, and spacious living areas. From Santa Rosa, it's an easy journey to reach stunning beaches like those at Sonoma Coast State Park, where travellers can enjoy sandy shores and dramatic cliffs.
What is the most popular type of holiday rental accomodation in Windsor?
In Windsor, holiday houses are the most popular type of accommodation, with about 25 available in the area. These properties often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also come with outdoor spaces, such as patios or gardens, superb for enjoying the pleasant California weather. Additionally, there are around 24 condos, which provide a more compact living option, typically including amenities like communal pools and fitness centres. There are also several apartments and villas, offering unique stays for those who prefer a different atmosphere.
Are there any family house rentals in Windsor?
In Windsor, California, there are numerous family-friendly house rentals available, with around 44 options spread throughout the area. This charming town offers a delightful blend of nature and community, making it an excellent choice for families. Many of these homes come equipped with spacious living areas, fully stocked kitchens for preparing meals together, and backyards where children can enjoy outdoor play.
Can I rent a holiday home with a pool or hot tub in Windsor?
In Windsor, California, there are several holiday homes available for rent that come with pools and hot tubs, with around 37 options to choose from. This charming town, situated in the heart of Sonoma County, offers a variety of properties set amidst stunning vineyards and scenic landscapes.

Travellers can expect amenities such as private swimming pools, relaxing hot tubs, outdoor patios for al fresco dining, and fully equipped kitchens superb for preparing meals with local ingredients. Many rentals also feature spacious living areas, barbecue facilities, and landscaped gardens, providing an ideal setting for families or groups looking to unwind after a day exploring the beautiful wine country.
Can I find long-stay holiday rentals in Windsor?
A long-stay holiday 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, travellers can find a variety of pet-friendly house rentals, with around 14 options available for those looking to enjoy a getaway with their furry companions. Many of these homes come equipped with desirable amenities such as spacious backyards, fully stocked kitchens, and comfortable living areas, ideal for families or groups.

The town is located in the picturesque Sonoma County, which offers beautiful parks and outdoor spaces great for walking pets, including the expansive Windsor Town Green. This area features walking paths, picnic areas, and frequent community events, making it a lively spot for both locals and visitors. Additionally, nearby parks like the Foothill Regional Park provide ample opportunities for hiking and exploring nature with pets on leashes.
Are there any remote work holiday rentals in Windsor?
In Windsor, California, there is a considerable selection of remote work holiday rentals available, with around 56 options to choose from. This charming town is set amidst the scenic Sonoma County wine region, providing a superb blend of work and leisure. Many properties come equipped with amenities tailored for remote work, including high-speed Wi-Fi, dedicated office spaces, ergonomic desks, and computer monitors, ensuring a productive environment for travellers needing to balance work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Windsor holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday 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 holiday rental?
October is the most popular time to visit Windsor, California, as the harvest season brings a vibrant atmosphere to this picturesque town, renowned for its wineries and charming landscapes. During this period, the weather is pleasantly warm, with average temperatures in the mid to high 20s Celsius, making it ideal for outdoor activities like wine tasting and exploring the scenic vineyards.

The peak season runs from August to October, attracting tourists eager to experience the beautiful fall colours and partake in various harvest festivals. Visitors can enjoy leisurely strolls through the vineyards, participate in wine tours, and savour local culinary delights at outdoor events.

If you're looking to make the most of your budget, consider visiting in November. This month often sees fewer crowds, allowing for a more relaxed experience while still enjoying the beautiful autumn scenery. Plus, local establishments may offer special deals as the tourist rush winds down.
How early should I book a Windsor holiday rental?
Book your Windsor holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Windsor?
In Windsor, visitors can enjoy a charming array of attractions and activities. The picturesque Windsor Town Green serves as the heart of the community, where holiday rentals nearby offer easy access to local events, farmers' markets, and outdoor concerts. The area is surrounded by lush parks, making it ideal for leisurely strolls or picnics.

Wine enthusiasts will appreciate the proximity to numerous vineyards and wineries in the surrounding Sonoma County, many of which offer tastings and tours just a short drive away. Additionally, the nearby Russian River provides opportunities for kayaking, canoeing, and enjoying the scenic beauty of the region.
Can I change or cancel my Windsor home rental booking on Vrbo?
To find Windsor holiday 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Windsor holiday 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.

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