Windsor Vacations from $229
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The Latest Windsor Vacation Packages
- The Marina Inn on San Francisco Bay
Sep 15 - Sep 17The Marina Inn on San Francisco Bay + Flight
San Leandro2 nights3.5 star property8.6/10 - Excellent (2,598 reviews)Roundtrip • Los Angeles (LAX) - Oakland (OAK)LAX - SFO • Nonstop SFO - LAX • Nonstop - The Setting Inn Napa Valley
Sep 17 - Sep 20The Setting Inn Napa Valley + Flight
Napa3 nights3.5 star property10/10 - Exceptional (326 reviews)"Amazing place, quiet, clean and so convient to Napa wineries and restaurants! 100% come back again!"Reviewed June 28, 2026Roundtrip • Dallas (DFW) - Oakland (OAK)DFW - SFO • Nonstop SFO - DFW • Nonstop - Claremont Resort & Club
Sep 20 - Sep 23Claremont Resort & Club + Flight
Claremont Hills3 nights5.0 star property9.0/10 - Wonderful (1,045 reviews)"History, location, amenities"Reviewed July 16, 2026Roundtrip • Burbank (BUR) - Oakland (OAK)BUR - OAK • Nonstop OAK - BUR • Nonstop - Brannan Cottage Inn
Sep 28 - Oct 1Brannan Cottage Inn + Flight
Calistoga3 nights3.0 star property9.6/10 - Exceptional (171 reviews)Roundtrip • Chicago (ORD) - Oakland (OAK)ORD - SFO • Nonstop SFO - ORD • Nonstop - Marquee By Avantstay Modern Stylish Estate w/ Pool & Entertainers Courtyard
Oct 8 - Oct 13Marquee By Avantstay Modern Stylish Estate w/ Pool & Entertainers Courtyard + Flight
Boyes Hot Springs5 nights3.5 star propertyRoundtrip • Chicago (ORD) - Oakland (OAK)ORD - OAK • 1 stop OAK - ORD • 1 stop
Discover the most popular places to visit in Windsor
What to do in Windsor
History Walking Tour of Healdsburg
Sebastopol: Guided Wine Tasting Experience with Sommelier
Sonoma County, CA: Outdoor Stargazing and Astronomy Tour
Windsor Hotel Deals
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Hampton Inn & Suites Windsor - Sonoma Wine Country
Hampton Inn & Suites Windsor - Sonoma Wine Country
Holiday Inn Windsor Wine Country by IHG
Holiday Inn Windsor Wine Country by IHG
Frequently Asked Questions
How much does a Windsor vacation package cost?
Offering great value package deals from $229 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?
November, December and January are great times to search for cheap Windsor vacation packages. Opting to travel in quieter months means you can usually find lower prices on hotels and flights.
How many days is enough for Windsor?
With a well-planned schedule, you can easily hit the main Windsor attractions in a handful of days. But if you want to discover lesser-known spots or go on day tours, think about booking your Windsor vacation for longer.
Is it worth booking a vacation package to Windsor?
It's easy to see why a Windsor vacation is on the to-do list of many travelers. Major attractions like Windsor Golf Club are just the beginning of things to keep you busy here.
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 your travel dates: What you'd like to do in Windsor and your preferred season can help you decide when to go.
- Set a budget: Factor in expenses such as food, flights and transportation when calculating how much to set aside for your trip to Windsor. Then, pick a property that fits your budget, whether that's a low-cost stay or a more luxurious getaway.
- Explore Windsor with our trip planning tool: Gain insights into the top attractions and best hotels for your trip to Windsor. You can also save your favorite places, collaborate with family and friends and manage all your plans in one place.
- Decide how many days away: Start by making a list of all the attractions you'd like to get to in Windsor. Then, estimate how long you'll need for each, along with any travel time.
- Bundle your accommodations and airfare: After you've nailed down your trip dates and duration, book the right Windsor vacation package for you.
- Book activities and experiences ahead of time: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on Windsor's best offerings. Find all the incredible things to do in Windsor in Windsor with our dedicated travel guide.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
If you're like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Windsor break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you spot them.
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Things to do near Windsor
Windsor, California, is perfect for an outdoor and romantic getaway, offering activities like golf and body treatments. Consider a day trip to explore local exhibits and attractions. Whether you're looking to hit the golf course or enjoy scenic views, Windsor has something for everyone. Don't miss the chance to experience the charm of this beautiful area.
Shopping
For unique gifts, visit Soda Rock Winery, only 8 miles from Windsor. If you're up for a drive, the Petaluma Village Premium Outlets, 22 miles away, offers a wide range of shops and entertainment options. Seed Bank, located 24 miles away, is worth checking out for specialty items.
Recreation
The Luther Burbank Center for the Arts offers an enriching cultural experience with performances that evoke romance and family vibes, located 5 miles from Windsor. For outdoor enthusiasts, the Wikiup Golf Course presents a vibrant sporting atmosphere, also 5 miles away. Enjoy adventure at the Redwood Empire Ice Arena, 7 miles from Windsor.
Adventure
Explore the lush grounds of Bohemian Grove, 11 miles from Windsor, for a unique camping experience. Hike the scenic Joe Rodota Trail, 9 miles away, perfect for outdoor enthusiasts. For family fun, visit Scandia Family Fun Center, 14 miles from Windsor, offering exciting arcade adventures and activities.
Nightlife
Experience the vibrant nightlife in Windsor with a visit to the Phoenix Theater, a lively nightclub located 24 miles away. Enjoy a mix of romance and entertainment, all while soaking in the city's energetic vibes for an unforgettable evening.
Find the best attractions near Windsor
Windsor, California, offers a delightful blend of outdoor beauty and romantic getaways. Visitors can explore picturesque spots like the piazza square, the scenic river, and nearby beaches. For those seeking culture and city experiences, attractions such as Windsor Castle and the Windsor Riverfront are must-see destinations. Whether you're looking for relaxation or adventure, Windsor has something to suit every traveler's taste.
- Healdsburg Plaza: Located 5 miles from Windsor, Healdsburg Plaza is a charming town square that captures the essence of local culture. Lined with boutique shops, art galleries, and cozy cafés, the plaza offers a vibrant atmosphere perfect for leisurely strolls, people-watching, and enjoying community events.
- Charles M. Schulz Museum: About 7 miles away, this museum celebrates the beloved creator of the Peanuts comic strip. With exhibits featuring original artwork and interactive displays, visitors can dive into the life and legacy of Charles M. Schulz while enjoying the whimsical world of Charlie Brown and friends.
- Sonoma County Fairgrounds: Situated 10 miles from Windsor, the fairgrounds host a variety of events, including fairs and concerts. This outdoor venue is ideal for family-friendly activities, offering a lively atmosphere where visitors can enjoy rides, games, and delicious food.
Best time to go to Windsor
The best time to visit Windsor is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is sunny with no rain. December is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.
Tips to save on your trip to Windsor
- Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
- Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Windsor.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.