Windsor holiday homes

We found 1,055 holiday rentals — enter your dates for availability
Select from 30 houses, 29 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:11 Dec - 18 Dec

Sunset or Sunrise with coffee in hand, hard to pick a favorite.
Stunning views of Russian River Valley from upper level of the house.
Living area
Our scenic dining room seats 8 together with 2 additional at the kitchen bar top
Exceptional
(182 reviews)

Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!

Healdsburg

8% off
NZ$6,621
for 7 nights, 1 home
NZ$946 per night
includes taxes & fees
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!
Wood Fired Pizza Oven
Interior
Outdoor Kitchen & Hot Tub
Property grounds
Exceptional
(329 reviews)

Wineberry Lodge, Gourmet In & Outdoor Kitchens & Spa

Sebastopol

8% off
NZ$8,594
for 7 nights, 1 home
NZ$1,228 per night
includes taxes & fees
Wineberry Lodge, Gourmet In & Outdoor Kitchens & Spa
Interior
Dining table
Master bedroom 1
Tasting room
Exceptional
(70 reviews)

Green Valley, Sonoma County Vacation Rental at a Working Winery.

Sebastopol

6% off
NZ$5,969
for 7 nights, 1 home
NZ$853 per night
includes taxes & fees
Green Valley, Sonoma County Vacation Rental at a Working Winery.
Interior
Interior
Terrace/patio
Pool
Exceptional
(21 reviews)

Modern Retreat - Spectacular View Home Above Dry Creek Valley

Healdsburg

8% off
NZ$17,309
for 7 nights, 1 home
NZ$2,473 per night
includes taxes & fees
Modern Retreat - Spectacular View Home Above Dry Creek Valley
Dining
Private kitchen
Pool
Dining
Exceptional
(202 reviews)

5 BEDROOM, 6.5 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE

Healdsburg

7% off
NZ$29,251
for 7 nights, 1 home
NZ$4,179 per night
includes taxes & fees
5 BEDROOM, 6.5 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
Enjoy a beautiful sunset by the firepit.
Dining room doors open to the outside patio for indoor/outdoor living.
Sauna
Dining room has wet bar, wine fridge, and ice machine.
Exceptional
(155 reviews)

Wine Country Escape: Luxury Estate, Pool, Sauna, Steam, Spa, Views, 5+ Bedrooms

Santa Rosa

8% off
NZ$34,330
for 7 nights, 1 home
NZ$4,904 per night
includes taxes & fees
Wine Country Escape: Luxury Estate, Pool, Sauna, Steam, Spa, Views, 5+ Bedrooms
Paths on the property
Large ranch-style home, 40-foot pool with full sun
Dining expands to seat 12
Seat 14 for dining by the pool!
Exceptional
(168 reviews)

Luxurious Large Home, Beautiful Pool, Extensive Gardens

Guerneville

12% off
NZ$14,206
for 7 nights, 1 home
NZ$2,029 per night
includes taxes & fees
Luxurious Large Home, Beautiful Pool, Extensive Gardens
Master Bedroom
Dining Room
Laundry Room
View from Pool
Exceptional
(60 reviews)

Architect Designed Wine Country View Home - Pool and Spa - Published in Magazine

Forestville

8% off
NZ$16,459
for 7 nights, 1 home
NZ$2,351 per night
includes taxes & fees
Architect Designed Wine Country View Home - Pool and Spa - Published in Magazine
Exterior
Front Porch
Living room
Kitchen
Exceptional
(258 reviews)

Blackberry Cottage located next to Wineberry Lodge

Sebastopol

8% off
NZ$4,202
for 7 nights, 1 home
NZ$600 per night
includes taxes & fees
Blackberry Cottage located next to Wineberry Lodge
✨Enjoy cooking together in the kitchen ✨
🍷🍇 Perfect getaway for those who want ✌️ and quiet
Warm & cozy feels ❤️
memories are made at the cabin Warm & cozy feels ❤️
Exceptional
(349 reviews)

✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

Healdsburg

8% off
NZ$3,288
for 7 nights, 1 cabin
NZ$470 per night
includes taxes & fees
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
18X36 Solar heated pool with locking cover. 2 shallow ends, sun all day
Redecorated: Flat screen TV, Fireplace, vineyard view
Separate Guest House - Queen bed, full bath w/shower, dedicated AC/Heat system.
'Mona Front View -spectacular sunsets & acres of vineyards on all sides
Exceptional
(165 reviews)

Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views

Healdsburg

8% off
NZ$13,761
for 7 nights, 1 home
NZ$1,966 per night
includes taxes & fees
Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views
Interior
Private kitchen
Dining
Room
Exceptional
(40 reviews)

A Peaceful Retreat in Wine Country - The Maefield Vineyard House

Forestville

8% off
NZ$14,835
for 7 nights, 1 home
NZ$2,119 per night
includes taxes & fees
A Peaceful Retreat in Wine Country - The Maefield Vineyard House
Living area
Interior
Kitchen Island
Terrace/patio
Exceptional
(12 reviews)

Gourmet Kitchen in Wine Country w/Hot Tub + Office

Windsor

8% off
NZ$13,995
for 7 nights, 1 home
NZ$1,999 per night
includes taxes & fees
Gourmet Kitchen in Wine Country w/Hot Tub + Office
Wonderful lighting
Fully equipped kitchen
Entryway to your Mary's Guest House
Private Redwood Deck
Exceptional
(81 reviews)

Elegant guest house within walking distance to fabulous downtown Sebastopol

Sebastopol

8% off
NZ$2,915
for 7 nights, 1 home
NZ$416 per night
includes taxes & fees
Elegant guest house within walking distance to fabulous downtown Sebastopol
Breakfast nook adjacent to kitchen. Extra chairs and high chair in garage.
Floor-to-ceiling windows in living room lets in light and views!
'River View' bedroom upstairs with Queen bed and adjoining deck.
Private outdoor shower with hot water on back deck under the redwood tree.
Exceptional
(172 reviews)

Zin and Zen on the River - Hot Tub, Kayaks, Dock, Bicycles and Views!

Guerneville

8% off
NZ$4,814
for 7 nights, 1 home
NZ$688 per night
includes taxes & fees
Zin and Zen on the River - Hot Tub, Kayaks, Dock, Bicycles and Views!
Games room
Dining
Property grounds
Terrace/patio
Exceptional
(46 reviews)

Wine Country Backyard Escape

Santa Rosa

7% off
NZ$6,453
for 7 nights, 1 home
NZ$922 per night
includes taxes & fees
Wine Country Backyard Escape
Majestic views and large windows in every room brings the outside in!
Enjoy our new, expanded outdoor living space.
View of the house from the front vineyard.
Enjoy the open floor plan.
Exceptional
(152 reviews)

Private 3-Acre Vineyard Estate with Extraordinary Views

Sebastopol

8% off
NZ$6,183
for 7 nights, 1 home
NZ$883 per night
includes taxes & fees
Private 3-Acre Vineyard Estate with Extraordinary Views
Interior
Outdoor dining
Exterior
Living area
Wonderful
(9 reviews)

Wine Country Estate Home

Santa Rosa

8% off
NZ$13,957
for 7 nights, 1 home
NZ$1,994 per night
includes taxes & fees
Wine Country Estate Home
Living room with slider to shady deck
Outdoor dining
Dining room with view to back deck and kitchen on right
Kitchen has all you need to prepare a meal for 6.
Exceptional
(177 reviews)

Comfortable Two Bedroom Two Bath shingled cottage in the West Sonoma wine region

Sebastopol

5% off
NZ$3,165
for 7 nights, 1 home
NZ$452 per night
includes taxes & fees
Comfortable Two Bedroom Two Bath shingled cottage in the West Sonoma wine region
Dinette that is ideal for morning light breakfasts
Front entry welcomes you along with radiant morning sun light
Front entry welcomes you along with radiant morning sun light
Pool
Exceptional
(28 reviews)

Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8

Santa Rosa

8% off
NZ$15,258
for 7 nights, 1 home
NZ$2,180 per night
includes taxes & fees
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8
Living room - north view
Large living + dinning area for family and friends to gather.
Front
Living room - south view
Exceptional
(50 reviews)

Wake Up in Your Own Private Vineyard - Healdsburg

Healdsburg

17% off
NZ$10,081
for 7 nights, 1 home
NZ$1,440 per night
includes taxes & fees
Wake Up in Your Own Private Vineyard - Healdsburg
Game room!
Room
Living area
Interior
Exceptional
(52 reviews)

Sonoma Valley Vacation Home

Santa Rosa

7% off
NZ$5,418
for 7 nights, 1 home
NZ$774 per night
includes taxes & fees
Sonoma Valley Vacation Home
Wood burning stove and pathway to hot tub gazebo
kitchen made for large dinner preperation
Private kitchen
Piano and accordion in living room
Exceptional
(88 reviews)

Grandma's House: Riverfront, Gorgeous View, Beach/Swimming/Canoeing Dog Friendly

Monte Rio

10% off
NZ$8,617
for 7 nights, 1 home
NZ$1,231 per night
includes taxes & fees
Grandma's House: Riverfront, Gorgeous View, Beach/Swimming/Canoeing Dog Friendly
View from the dock area
Kicthen
Livingroom
More views from the deck
Exceptional
(87 reviews)

Robin's Hood on the River w/ Spectacular Views, near vineyards & coastal beaches

Guerneville

19% off
NZ$5,084
for 7 nights, 1 home
NZ$726 per night
includes taxes & fees
Robin's Hood on the River w/ Spectacular Views, near vineyards & coastal beaches

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • Windsor Golf Club (1.5 mi / 2.4 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)
  • 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)
  • Safari West (6.6 mi / 10.6 km)
  • Old Courthouse Square (9.2 mi / 14.9 km)
  • Petrified Forest (9.6 mi / 15.5 km)
  • Armstrong Redwoods State Park (10.1 mi / 16.3 km)
  • Johnson's Beach (10.3 mi / 16.7 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 considering a holiday rental in Windsor, California, the charming neighbourhood of Downtown Windsor is an excellent choice. This area boasts a variety of properties, from cosy cottages to spacious family homes, suiting different preferences and budgets. Staying here places you within walking distance of delightful local attractions, such as the Windsor Town Green, a lovely park featuring a pond, picnic areas, and a vibrant community atmosphere. Additionally, the nearby Russian River offers opportunities for outdoor activities like kayaking and cycling, making it a fantastic spot for nature enthusiasts.Another appealing area is the nearby Windsor Golf Club, which not only provides stunning views but also easy access to the picturesque Sonoma County wine country. This region is renowned for its award-winning wineries and vineyards, great for those looking to explore local wine tasting experiences.
What is the most popular type of holiday rental accomodation in Windsor?
In Windsor, holiday houses are the most popular type of holiday rental, with around 76 available in the area. These homes typically provide spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking comfort during their stay. Many also feature outdoor spaces such as gardens or patios, superb for relaxing after a day of exploring the surroundings. Condominiums and apartments are also common, with approximately 44 of each type, appealing to those looking for a more compact option without sacrificing amenities.
Are there any family house rentals in Windsor?
In Windsor, California, there are some family-friendly house rentals available, with approximately 23 options to choose from. This charming town is located in Sonoma County, renowned for its picturesque vineyards and proximity to various outdoor activities. Many of the properties feature spacious living areas, fully equipped kitchens, and outdoor spaces ideal for family gatherings or barbecues.Guests can enjoy amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay. The locale is close to scenic parks like Windsor Town Green, which offers playgrounds and open spaces for children to explore. Additionally, the nearby Russian River provides opportunities for kayaking and picnicking, making Windsor an excellent choice for families seeking a blend of relaxation and adventure.
Can I rent a holiday home with a pool or hot tub in Windsor?
In Windsor, California, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 29 options to choose from. This charming town, located in Sonoma County, offers a serene atmosphere surrounded by beautiful vineyards and picturesque landscapes. Many of these properties include amenities such as private swimming pools, relaxing hot tubs, and spacious outdoor areas superb for entertaining or family gatherings.Travellers can also expect fully equipped kitchens, comfortable living spaces, and some rentals may offer additional features like barbecue facilities and fire pits, enhancing the experience of enjoying the warm Californian weather.
Are there pet-friendly house rentals in Windsor?
In Windsor, there are several pet-friendly house rentals available for travellers seeking a comfortable stay. Many of these properties typically feature spacious layouts, fully equipped kitchens, and outdoor areas such as gardens or patios, allowing pets to roam freely. The homes are often designed with amenities like laundry facilities, Wi-Fi, and inviting living spaces to ensure a pleasant experience for guests.The neighbourhood itself is family-friendly and offers a variety of parks where pets can enjoy the outdoors. The nearby Windsor Town Green is a lovely spot, featuring walking paths and open spaces ideal for leisurely strolls with pets. Additionally, the surrounding Sonoma County area is known for its scenic vineyards and wineries, many of which are pet-friendly, providing opportunities for wine tasting while enjoying the company of your furry friends.
Are there any remote work holiday rentals in Windsor?
In Windsor, California, there are numerous options for remote work holiday rentals, with around 152 available throughout the area. This charming town offers a blend of natural beauty and modern conveniences, making it an ideal spot for those looking to work remotely. Many properties feature essential amenities such as free Wi-Fi, ensuring you stay connected during your work hours.Travellers can expect a variety of accommodations, including spacious homes with dedicated workspaces, comfortable living areas, and fully equipped kitchens, allowing for a productive and enjoyable stay. The surrounding regional parks and the scenic Russian River provide opportunities for leisure activities after work, with options for hiking, biking, and exploring the local vineyards. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Windsor?
In Windsor, popular holiday rentals typically feature a range of amenities to enhance the stay experience. Most properties come equipped with kitchens, allowing guests to prepare their own meals and enjoy the convenience of home cooking. Many rentals also include outdoor decks or patios, great for relaxing and enjoying the pleasant California weather. Additionally, a coffee and tea maker is commonly provided, suiting those who appreciate a warm beverage at any time. For added comfort, many accommodations have fireplaces, creating a cosy atmosphere, especially during cooler evenings. Onsite parking is also a common amenity, making it convenient for guests with vehicles.
When is the best time to visit Windsor for a holiday rental?
The best time to visit Windsor for a holiday rental is during the peak season from August to October, with October being particularly popular. This charming town in California is a prime destination for wine enthusiasts and outdoor adventurers alike, as the vineyards are bursting with activity during the harvest season. The warm, sunny days, typically ranging from 15 to 25 degrees Celsius, create an inclusive setting for exploring the beautiful wineries and enjoying outdoor activities.October offers a unique opportunity to experience the vibrant autumn colours in the surrounding landscapes, making it a superb time for leisurely walks or bike rides through the scenic vineyards. The pleasant weather also allows for al fresco dining at local restaurants, where you can savour delicious farm-to-table cuisine paired with exquisite local wines.For those who are looking to travel on a budget, consider planning your visit in November. While this month falls outside the bustling tourist season, it still holds its own charm, featuring a peaceful ambiance and the chance to enjoy the last remnants of autumn while avoiding large crowds.
What are the top attractions in Windsor?
In Windsor, California, visitors can explore a variety of attractions that highlight the area's natural beauty and local culture. The Windsor Town Green is a central hub featuring a scenic park, walking paths, and a variety of events throughout the year, making it a lovely spot for relaxation and community gatherings. Nearby, the Russian River offers opportunities for kayaking, fishing, and picnicking along its banks, appealing to outdoor enthusiasts.Wine lovers will appreciate the proximity to the renowned Sonoma County wine region, with several vineyards and tasting rooms just a short drive away. The nearby Oliver's Market is a great place for local produce and gourmet foods, adding to the culinary experience of the area.For those seeking a bit of adventure, the nearby Foothill Regional Park offers hiking trails, picnic areas, and beautiful views, great for a day out in nature. Additionally, the historic Windsor Historical Society provides insights into the town's past and showcases local heritage.
Are all fees included in the Windsor holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Windsor holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Windsor holiday homes?
You can find great discounts on holiday homes in Windsor on Bookabach, 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.
Can I change or cancel my Windsor holiday home booking on Bookabach?
To find Windsor holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Windsor?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Windsor holiday home?
Book your Windsor holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Windsor?
Prices for holiday homes 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. Bookabach offers something for every taste and budget, from affordable homes in Windsor to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 as applicable. 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.