Windsor holiday lettings

We found 1,059 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:8 Jan - 15 Jan

Terrace/patio
Living area
Private kitchen
Living area
Excellent
(6 reviews)

Vineyard Villa: Pool/Spa | Pickleball/Tennis | Dog

Santa Rosa

8% off
£4,748
for 7 nights, 1 villa
£678 per night
includes taxes & fees
Vineyard Villa: Pool/Spa | Pickleball/Tennis | Dog
Games room
Room
Outdoor dining
Private kitchen
Exceptional
(47 reviews)

Wine Country Backyard Escape

Santa Rosa

7% off
£2,747
for 7 nights, 1 home
£392 per night
includes taxes & fees
Wine Country Backyard Escape
Room
Private kitchen
Exterior
Interior
Exceptional
(41 reviews)

A Peaceful Retreat in Wine Country - The Maefield Vineyard House

Forestville

8% off
£6,465
for 7 nights, 1 home
£924 per night
includes taxes & fees
A Peaceful Retreat in Wine Country - The Maefield Vineyard House
Living area
Outdoor dining
Interior
Exterior
Wonderful
(9 reviews)

Wine Country Estate Home

Santa Rosa

8% off
£6,104
for 7 nights, 1 home
£872 per night
includes taxes & fees
Wine Country Estate Home
Pull up a stool & savor your favorite meal or drink at our chic kitchen counter.
Begin your day with a view that takes your breath away - simply stunning.
Stroll the scenic pathway from house to garden and golf area.
Fun awaits: Follow the stairs downstairs for exciting entertainment!
Exceptional
(9 reviews)

Russian River Redwoods: Hot Tub, Fire Pit, Dogs OK

Forestville

8% off
£1,933
for 7 nights, 1 home
£276 per night
includes taxes & fees
Russian River Redwoods: Hot Tub, Fire Pit, Dogs OK
Unwind and reconnect with loved ones in the comfort of our inviting indoor space.
Sit, Sip, and Savor with Vineyard Views - Perfect Outdoor Seating!
Sweet dreams are made of this! Sink into our cozy linens and drift off into dreamland in style.
Get cooking in style! Check out our chef's kitchen and cozy kitchen seating area.
Exceptional
(6 reviews)

Vineyard View: Spa | Fire-pit | Dog Friendly

Sebastopol

8% off
£3,545
for 7 nights, 1 home
£506 per night
includes taxes & fees
Vineyard View: Spa | Fire-pit | Dog Friendly
Dining
Private kitchen
Pool
Dining
Exceptional
(205 reviews)

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

Healdsburg

6% off
£13,338
for 7 nights, 1 home
£1,905 per night
includes taxes & fees
5 BEDROOM, 6.5 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
Paths on the property
Large ranch-style home, 40-foot pool with full sun
Welcome to Valley Lane Retreat!
Seat 14 for dining by the pool!
Exceptional
(170 reviews)

Luxurious Large Home, Beautiful Pool, Extensive Gardens

Guerneville

12% off
£6,346
for 7 nights, 1 home
£907 per night
includes taxes & fees
Luxurious Large Home, Beautiful Pool, Extensive Gardens
The other kitchen view
Welcome home!
Living room
Swim at Ives Pool, just two blocks away! Reservations now required ivespool.org
Exceptional
(197 reviews)

Spacious Sebastopol Home - 5-Minute Walk to Town, Wine Country at Your Doorstep

Sebastopol

8% off
£1,754
for 7 nights, 1 home
£251 per night
includes taxes & fees
Spacious Sebastopol Home - 5-Minute Walk to Town, Wine Country at Your Doorstep
Terrace/patio
Kitchen Island
Interior
Living area
Exceptional
(14 reviews)

Gourmet Kitchen in Wine Country w/Hot Tub + Office

Windsor

8% off
£6,120
for 7 nights, 1 home
£874 per night
includes taxes & fees
Gourmet Kitchen in Wine Country w/Hot Tub + Office
Dining and Kitchen Open Concept off the Deck to BBQ
Great Location for Walking to River, Beach, & Town over the Pedestrian Bridge
Welcome To Vista Serena Drive thru the Gate to Home
Living Great Room facing towards Deck with Hot Tub
Exceptional
(308 reviews)

PRIME LOCATION Private,Spacious+AC -2blk to Town/River/Beach+SPA+Tennis/Kid Park

Guerneville

7% off
£2,676
for 7 nights, 1 home
£382 per night
includes taxes & fees
PRIME LOCATION Private,Spacious+AC -2blk to Town/River/Beach+SPA+Tennis/Kid Park
Fun bar we made ourselves out of reclaimed redwood from the property.
Doors leading out from living room to back porch.
Cozy fireplace and tv with netflix.
Large double doors go out to expansive back deck.
Exceptional
(13 reviews)

Wine Country Russian River~Local Beach~Kayaks Incl~Hot tub~Outdoor Bar~ Families

Guerneville

7% off
£3,820
for 7 nights, 1 home
£546 per night
includes taxes & fees
Wine Country Russian River~Local Beach~Kayaks Incl~Hot tub~Outdoor Bar~ Families
Outdoor Kitchen & Hot Tub
Interior
Kitchen
Property grounds
Exceptional
(331 reviews)

Wineberry Lodge, Gourmet In & Outdoor Kitchens & Spa

Sebastopol

7% off
£3,912
for 7 nights, 1 home
£559 per night
includes taxes & fees
Wineberry Lodge, Gourmet In & Outdoor Kitchens & Spa
Interior
Living area
Living area
Property grounds
Exceptional
(50 reviews)

Stunning Contemporary Home, a River Penthouse on Russian River, like No Other!!

Monte Rio

8% off
£6,431
for 7 nights, 1 home
£919 per night
includes taxes & fees
Stunning Contemporary Home, a River Penthouse on Russian River, like No Other!!
Separate Guest House - Queen bed, full bath w/shower, dedicated AC/Heat system.
Redecorated: Flat screen TV, Fireplace, vineyard view
Dining Room - Seats 8-10 - doors open to porch, outdoor table & sunset views
18X36 Solar heated pool with locking cover. 2 shallow ends, sun all day
Exceptional
(165 reviews)

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

Healdsburg

8% off
£5,875
for 7 nights, 1 home
£839 per night
includes taxes & fees
Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views
Terrace/patio
Interior
Pool
Pool
Exceptional
(21 reviews)

Modern Retreat - Spectacular View Home Above Dry Creek Valley

Healdsburg

8% off
£7,866
for 7 nights, 1 home
£1,124 per night
includes taxes & fees
Modern Retreat - Spectacular View Home Above Dry Creek Valley
Living area
Pool
Exterior
Property grounds
Exceptional
(34 reviews)

Cozy Wine Country Guesthouse with Private Pool & Yard

Santa Rosa

9% off
£1,873
for 7 nights, 1 home
£268 per night
includes taxes & fees
Cozy Wine Country Guesthouse with Private Pool & Yard
Elevate your dining experience with our charming outdoor seating!
TV time just got better! Catch your favorite shows on our big screen.
Find peace and relaxation in our tranquil tree-surrounded home!
Feast and relax in one place - our dining table just steps away living area!
Exceptional
(11 reviews)

Tariff Discount: Romantic Retreat w/ Spa

Forestville

7% off
£1,418
for 7 nights, 1 home
£203 per night
includes taxes & fees
Tariff Discount: Romantic Retreat w/ Spa
The large, open kitchen with amazing views invites cooking and dining in.
Enjoy our new, expanded outdoor living space.
Majestic views and large windows in every room brings the outside in!
View of the house from the front vineyard.
Exceptional
(152 reviews)

Private 3-Acre Vineyard Estate with Extraordinary Views

Sebastopol

8% off
£2,472
for 7 nights, 1 home
£353 per night
includes taxes & fees
Private 3-Acre Vineyard Estate with Extraordinary Views
Tasting room
Dining table
Interior
Master bedroom 1
Exceptional
(70 reviews)

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

Sebastopol

6% off
£2,638
for 7 nights, 1 home
£377 per night
includes taxes & fees
Green Valley, Sonoma County Vacation Rental at a Working Winery.
Dining
Property grounds
Terrace/patio
Room
Exceptional
(15 reviews)

Wine Country California Zen Home , beautiful & Unique with stunning setting.

Santa Rosa

8% off
£2,046
for 7 nights, 1 home
£292 per night
includes taxes & fees
Wine Country California Zen Home , beautiful & Unique with stunning setting.
Interior
Terrace/patio
Room
Exterior
Exceptional
(14 reviews)

Adorable 1 BD 1 BA in one of SR's best neighborhoods!

Santa Rosa

9% off
£1,406
for 7 nights, 1 cottage
£201 per night
includes taxes & fees
Adorable 1 BD 1 BA in one of SR's best neighborhoods!
Terrace/patio
Living area
Room
Exterior
Exceptional
(66 reviews)

Pet Friendly Vacation Wonderland On Dutch Bill Creek 1 Mile To Monte Rio Beach

Occidental

11% off
£1,681
for 7 nights, 1 home
£240 per night
includes taxes & fees
Pet Friendly Vacation Wonderland On Dutch Bill Creek 1 Mile To Monte Rio Beach
View from Pool
Dining Room
Master Bedroom
View from porch
Exceptional
(61 reviews)

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

Forestville

8% off
£7,490
for 7 nights, 1 home
£1,070 per night
includes taxes & fees
Architect Designed Wine Country View Home - Pool and Spa - Published in Magazine

  • 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, 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)
  • 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 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)
  • 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)

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.
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.
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.
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, 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 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 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.
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, 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.
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 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 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.
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 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.
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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