Windsor Holidays
Book a Hotel + Flight or Car together to unlock savings
Windsor Holiday
Our pick of the best Windsor Hotel Deals
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane Windsor CA
Fully refundable
NZ$236
23 Aug - 24 Aug
includes taxes & fees
Hampton Inn & Suites Windsor - Sonoma Wine Country
8937 Brooks Road South Windsor CA
Fully refundableReserve now, pay when you stay
NZ$284
16 Aug - 17 Aug
includes taxes & fees
9.2/10 Wonderful! (1,015 reviews)
"The part we liked the best was they had a heated pool, so even at night it was enjoyable. I would come back for the pool. Staff was friendly and helpful. The room was nice and newly renovated. Everything was clean except we did notice a bit of black mold in the corner of the shower, not sure how ..."
Reviewed on 10 Aug 2026
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy Windsor CA
Fully refundable
NZ$246
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (1,067 reviews)
"Clean and comfortable room"
Reviewed on 10 Aug 2026
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.
Stay near popular Windsor attractions
Russian Hill Estate Vineyards
9.6/10 (4 reviews)
Russian Hill Estate crafted acclaimed Pinot Noir and Syrah from Sonoma's Russian River Valley terroir. Visitors enjoyed intimate tastings with vineyard views and picnic areas perfect for savouring their distinctive wines.
Windsor Golf Club
8.8/10 (19 reviews)
Enjoy a round of golf in Windsor at Windsor Golf Club. Stroll along the area's riverfront or simply savour its top-notch restaurants.
La Crema Estate at Saralee's Vineyard
You can enjoy a tasting or tour at La Crema Estate at Saralee's Vineyard during your travels to Windsor. Visit the wineries or top-notch restaurants in this family-friendly area.
Pacific Coast Air Museum
10.0/10 (4 reviews)
The Pacific Coast Air Museum displays meticulously preserved aircraft spanning decades of aviation history. Climb into cockpits during "Open Cockpit Day" events for a pilot's perspective.
Windsor Oaks Vineyards
9.6/10 (5 reviews)
You can enjoy a tasting or tour at Windsor Oaks Vineyards during your travels to Windsor. Stroll along the riverfront in this family-friendly area or visit its top-notch restaurants.
Dom Whitney Tasting Lounge
8.6/10 (4 reviews)
This Windsor wine sanctuary showcases multiple local wineries under one welcoming roof. Knowledgeable staff guide you through diverse regional varietals while sharing insights about Sonoma's winemaking heritage.
Martinelli Vineyard
8.6/10 (4 reviews)
Housed in a historic hop barn, Martinelli Winery showcases five generations of family winemaking expertise. Sample their estate-grown Pinot Noir and Zinfandel while learning about 135 years of viticultural heritage.
Guerro Fernandez
You can enjoy a tasting or tour at Guerro Fernandez during your travels to Windsor. Visit the top-notch restaurants or wineries in this family-friendly area.
What to do in Windsor
Calaveras Wine Tour - Self-Guided Audio Experience
NZ$51
per traveller
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
NZ$86
per adult
86% of travellers recommend
Frequently asked questions
How much does a Windsor holiday package cost?
Offering great value package deals 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?
- 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.
- 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.
- 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.
- 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.
