Windsor Vacations
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Find the Best Windsor Vacation Packages
Windsor Hotel Deals
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane Windsor CA
Fully refundable
￥18,256
￥20,811 total
Oct 25 - Oct 26
includes taxes & fees
9.2/10 Wonderful! (1,306 reviews)
"the breakfast buffet was very good and the staff were very professional."
Reviewed on Sep 22, 2026
Hampton Inn & Suites Windsor - Sonoma Wine Country
8937 Brooks Road South Windsor CA
Fully refundableReserve now, pay when you stay
￥23,301
￥26,608 total
Oct 25 - Oct 26
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Air conditioning was very loud"
Reviewed on Sep 20, 2026
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy Windsor CA
Fully refundable
￥20,796
￥23,708 total
Oct 26 - Oct 27
includes taxes & fees
9/10 Wonderful! (1,066 reviews)
"El personal es amable"
Reviewed on Sep 24, 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 savoring their distinctive wines.
Windsor Golf Club
8.8/10 (19 reviews)
This championship course winds through Sonoma wine country, challenging golfers with scenic water hazards and majestic oaks. Enjoy innovative cuisine at Charlie's Restaurant overlooking the countryside.
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.
La Crema Estate at Saralee's Vineyard
This historic barn-turned-tasting room showcases La Crema's acclaimed cool-climate wines in Russian River Valley. Savor vineyard views while experiencing guided tastings or specialty pairings.
Windsor Oaks Vineyards
9.6/10 (5 reviews)
This estate produces premium wines across three appellations, with various grapes thriving in diverse microclimates. Visit during exclusive open days to savor handcrafted wines amid preserved natural beauty.
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.
Powell's Sweet Shoppe - Windsor
10.0/10 (7 reviews)
Powell's Sweet Shoppe transported visitors to a candy wonderland with nostalgic treats and vintage toys. The shop's continuous playing of "Charlie and the Chocolate Factory" created a whimsical atmosphere for all ages.
Guerro Fernandez
You can enjoy a tasting or tour at Guerro Fernandez during your travels to Windsor. Check out the wineries or top-notch restaurants in this family-friendly area.
What to do in Windsor
Sonoma County Wine Tour: Self-Guided GPS Audio Driving Guide
￥4,745
per traveler
Sonoma Horseback-Riding Tour
￥20,652
per adult
100% of travellers recommend
Frequently asked questions
How much does a Windsor vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation 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 vacation package, consider visiting in December, January and February. You'll typically find better rates on accommodations and flights during these months — perfect for travelers wishing to save money.
How many days is enough for Windsor?
The ideal length of your Windsor vacation 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 vacation package to Windsor?
Windsor is a good vacation 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 vacation 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 vacation package as early as possible.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your next Windsor getaway by booking a personalized vacation 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 vacation package to Windsor?
If you have your Windsor vacation 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 traveling 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 accommodations, 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 accommodations and airfare: Once you've settled on your dates and duration, book the ideal Windsor vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
