Luxury Vacation Rentals in Windsor

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 6 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Windsor

Station House

4 bedrooms•3.5 baths

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New

~$190 less than other sites

Boho Betty

4 bedrooms•2.5 baths

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New

~$1,240 less than other sites

Windsor Wildflower

3 bedrooms•2 baths

•

New

~$115 less than other sites

Luxury

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting

3 bedrooms•4 baths

•

~$280 less than other sites

Spacious Santa Rosa Retreat - Outdoor Kitchen, Pool, Spa

4 bedrooms•3 baths

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~$295 less than other sites

Bird and Barrel Vineyard Farmhouse - Healdsburg Wine Country Retreat with Game Barn

3 bedrooms•2 baths

•

New

~$95 less than other sites

Welcome to Windsor

Meet a higher standard for wine country stays with our luxury vacation rentals in Windsor. Set amid Sonoma’s rolling vineyards, each Wander home blends five-star consistency with the privacy of a beautifully designed residence.

Expect hotel-grade amenities at every turn. Ultrafast WiFi for effortless work, chef-ready kitchens, plush mattresses with premium linens, many with private pools or hot tubs, plus outdoor spaces for golden-hour lounging. Every stay includes pristine cleaning and 24/7 concierge service, so you can focus on time together, not logistics.

Destinations near Windsor

Available soon in Windsor

Station House

4 bedrooms•3.5 baths

•

New

~$190 less than other sites

Windsor Wildflower

3 bedrooms•2 baths

•

New

~$115 less than other sites

Luxury

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting

3 bedrooms•4 baths

•

~$280 less than other sites

Spacious Santa Rosa Retreat - Outdoor Kitchen, Pool, Spa

4 bedrooms•3 baths

•

~$295 less than other sites

Bird and Barrel Vineyard Farmhouse - Healdsburg Wine Country Retreat with Game Barn

3 bedrooms•2 baths

•

New

~$95 less than other sites

All homes in Windsor

Station House

4 bedrooms•3.5 baths

•

New

~$190 less than other sites

Boho Betty

4 bedrooms•2.5 baths

•

New

~$1,240 less than other sites

Windsor Wildflower

3 bedrooms•2 baths

•

New

~$115 less than other sites

Luxury

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting

3 bedrooms•4 baths

•

~$280 less than other sites

Spacious Santa Rosa Retreat - Outdoor Kitchen, Pool, Spa

4 bedrooms•3 baths

•

~$295 less than other sites

Bird and Barrel Vineyard Farmhouse - Healdsburg Wine Country Retreat with Game Barn

3 bedrooms•2 baths

•

New

~$95 less than other sites

View all homes

Highlights in Windsor

Discover a charming Sonoma County getaway featuring world-class wineries, scenic regional parks, and a vibrant, family-friendly town green.

Windsor Town Green

Foothill Regional Park

Kendall-Jackson Wine Estate & Gardens

Sonoma-Cutrer Vineyards

Steelhead Beach Regional Park

Windsor Golf Club

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for vacation rentals in Windsor

Other popular amenities & vacation types in Windsor

Private pool vacation rentals in Windsor

Discover more of Windsor

Anchored by the Town Green, Windsor offers a relaxed base in the heart of Sonoma. Vine-covered hills surround the village, the Russian River meanders nearby, and celebrated valleys like Dry Creek and Alexander are minutes away.

Visit for spring blooms, long summer evenings beneath oak trees, or the energy of harvest each fall. Redwoods, river bends, and the Sonoma Coast are close enough for effortless day trips. This blend of small-town warmth and world-class wine country is why Wander's luxury vacation rentals in Windsor are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Windsor

Why should I book a Wander in Windsor over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Windsor delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Windsor?

Some of our most popular vacation rentals in Windsor include Station House, Boho Betty, and Windsor Wildflower. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Windsor?

Wander offers 6 vacation rentals in Windsor, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Windsor?

You can check-in to Wander vacation rentals in Windsor after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Windsor have WiFi access?

Yes. Every Wander home in Windsor has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.