Windsor Holidays from AU$3,015

Book a Hotel + Flight or Car together to unlock savings

Photo by Rick Alvarez

Your Windsor Holiday

Get to know the picturesque city of Windsor with a tailor-made Windsor holiday package and immerse yourself in the very best it can offer. From its lively atmosphere and cultural experiences to its spectacular views, prepare to fall for the unique charms of this exciting destination. You'll want to go sightseeing during your trip to Windsor. Don't miss top attractions such as Kendall-Jackson Wine Estate and Gardens, Healdsburg Plaza and Luther Burbank Centre for the Arts. Expedia will help you escape the everyday. Tailor your holiday to Windsor to match your travel style, whatever that may be!

The Latest Windsor Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Vino Bello Resort

Vino Bello Resort

4 out of 5
Soscol Gateway South
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Sydney (SYD) to Oakland (OAK)
8.4/10 Very Good! (1,001 reviews)
Beautiful property. Spacious and clean.

Reviewed on 28 Jul. 2025

Syrah by Avantstay Hilltop Haven in Sonoma Private Pool + Patio

Syrah by Avantstay Hilltop Haven in Sonoma Private Pool + Patio

4 out of 5
Save 100% on your flight
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Sydney (SYD) to Oakland (OAK)
6/10 (1 review)
Inn At Sonoma - A Four Sisters Inn

Inn At Sonoma - A Four Sisters Inn

3.5 out of 5
Save 100% on your flight
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Sydney (SYD) to Oakland (OAK)
8.8/10 Excellent! (1,000 reviews)
The In is very nice. However it lacks some basic amenities. There is no in-room safe. They will hold valuables at the front desk safe but only up to $1000 in value. The lighting in the room leaves something to be desired. A dimmer would have been nice. The counter space in the bathroom is very tight. Two people would have a tough time placing belonging. The fireplace is very nice. Just know there is no view but you are in downtown Sonoma so that should be expected. If you like to cook, buy their cookbook. The breakfast is very nice. It is vegetarian, no meat but lovely choices.

Reviewed on 26 Jul. 2025

The Lodge at Sonoma Resort, Autograph Collection

The Lodge at Sonoma Resort, Autograph Collection

4 out of 5
Save 100% on your flight
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Sydney (SYD) to Oakland (OAK)
8.6/10 Excellent! (654 reviews)
Exhorbitant resort fee. Rip off all around

Reviewed on 29 Jul. 2025

Carneros Resort and Spa

Carneros Resort and Spa

5 out of 5
Save 100% on your flight
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Sydney (SYD) to Oakland (OAK)
9.2/10 Wonderful! (339 reviews)
Our stay was amazing! The room and property are gorgeous! The staff was friendly and helpful and attentive. We look forward to our next stay!

Reviewed on 29 Jul. 2025

Windsor Holiday

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sonoma County Airport (STS)
Population
27,500
Max Temp Winter
16ºC
Max Temp Summer
27ºC
Top Sights
Safari West, Francis Ford Coppola Winery and Armstrong Redwoods State Park

Our pick of the best Windsor Hotel Deals

Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG

3 out of 5
8755 Old Redwood Hwy, Windsor, CA
Fully refundable
The price is AU$190 per night from 3 Aug to 4 Aug
AU$190
3 Aug - 4 Aug
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"New clean convient"

Reviewed on 30 Jul. 2025

Holiday Inn Windsor Wine Country by IHG
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

2.5 out of 5
8865 Conde Lane, Windsor, CA
Fully refundable
The price is AU$211 per night from 3 Aug to 4 Aug
AU$211
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (1,083 reviews)
"Vehicle was gated in and safe."

Reviewed on 29 Jul. 2025

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 out of 5
8937 Brooks Road South, Windsor, CA
Fully refundableReserve now, pay when you stay
The price is AU$233 per night from 20 Aug to 21 Aug
AU$233
20 Aug - 21 Aug
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Very clean! Extremely friendly staff."

Reviewed on 30 Jul. 2025

Hampton Inn & Suites Windsor - Sonoma Wine Country
See all 2,111 properties in Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
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Cheap Holidays
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beach holidays
Beach Holidays
Beach Holidays

What to do in Windsor

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

AU$77
per adult
84% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Self Guided Audio Driving Tour from Vancouver to Whistler

Self-Guided Audio Driving Tour of Sonoma and Napa Valley

AU$26
per traveller
Self-Guided Audio Driving Tour of Sonoma and Napa Valley
Healdsburg Wine and Food Pairing Walking Tour

Healdsburg Wine and Food Pairing Guided Walking Tour

AU$212
per adult
96% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
See all activities in Windsor

Frequently asked questions

How much does a Windsor holiday package cost?
Offering great value package deals from AU$3,015 on Expedia, you'll be pleasantly surprised at how much a holiday to Windsor costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Windsor?
If you'd like to score a cheap Windsor holiday package, consider visiting in December, January and February. You'll typically find better rates on accommodation and flights during these months — perfect for travellers wishing to save money.
How many days is enough for Windsor?
The ideal length of your Windsor holiday depends on what you'd like to do. Typically, a few days to a week will give you time to go to all the top sights and explore some hidden treasures along the way.
Is it worth booking a holiday package to Windsor?
Windsor is a good holiday destination with attractions like Windsor Golf Club among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Windsor holiday promises a good time for everyone.
How to find the best Windsor package deals?
Use Expedia's handy filters to find some fabulous Windsor package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Windsor package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package as early as possible.
Is it cheaper to book a Windsor holiday as a package?
You can enjoy significant savings on your next Windsor getaway by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to view the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Windsor?
If you have your Windsor holiday dates locked in, book as early as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Windsor?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Windsor.
  2. Budget wisely: On top of the price of your accommodation, you'll need to consider other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected expenses that could arise during your trip to Windsor.
  3. Work out your trip length: Think about how long you want to spend discovering Windsor. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your accommodation and airfare: Once you've settled on your dates and duration, book the ideal Windsor holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.