How much does a Windsor vacation package cost?

Offering great value package deals from $511 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.

Windsor Vacation Packages 2025/2026 from $524

Your Windsor Vacation

Uncover the best parts of Windsor with a customized Windsor vacation package. From its lively atmosphere and cultural experiences to its spectacular views, you'll love experiencing this picturesque city the way you want to. Like to start exploring your surroundings? Windsor Golf Club, Sonoma-Cutrer Vineyards Cutrer Vineyard and Windsor Oaks Vineyards are three of the top places to visit during a trip to Windsor. Browse Expedia's wide range of travel options and start planning your ideal vacation to Windsor now.

The Latest Windsor vacation packages

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

RiverPointe Napa Valley Resort

Stonehouse

Save 100% on your flight

$511

per person

Oct 4 - Oct 7

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Oakland (OAK)

8.8/10 Excellent! (1,297 reviews)

Clean and ready for early checkin

Reviewed on Aug 23, 2025

MacArthur Place Hotel & Spa

Save 100% on your flight

$3,778

per person

Oct 17 - Oct 22

found 1 hour ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Oakland (OAK)

9.4/10 Exceptional! (827 reviews)

Maybe one of the finest hotels I have ever stayed out. Outstanding on all fronts.

Reviewed on Aug 21, 2025

Claremont Resort & Club

Claremont Hills

Save 100% on your flight

$734

per person

Oct 24 - Oct 27

found 4 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Oakland (OAK)

8.8/10 Excellent! (1,014 reviews)

Wonderful room, view, comfortable bed, friendly staff, beautiful pools and tennis courts. It’s a lovely property.

Reviewed on Aug 23, 2025

Silverado Resort

Save 100% on your flight

$1,296

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Oakland (OAK)

8.8/10 Excellent! (1,029 reviews)

Well managed friendly staff. Our condo over looked the 7th fairway. Beautiful grounds.

Reviewed on Aug 21, 2025

WorldMark Windsor

Save 100% on your flight

$559

per person

Oct 29 - Nov 2

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Oakland (OAK)

9/10 Wonderful! (329 reviews)

Loved this property! Stayed with my Fiance! Great for family ❤️ Only wished the hot tubs were fixed & WiFi should be free 😊 other than that, great stay. Staffs were very accommodative and informative. We had Dante that introduced us to the nearby restaurants and what to do around the area. Greatly appreciated.

Reviewed on Apr 27, 2025

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Windsor Hotel Deals

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

8865 Conde Lane, Windsor, CA

Fully refundable

$118 nightly

$135 total

Aug 26 - Aug 27

Total with taxes and fees

9.2/10 Wonderful! (1,135 reviews)

"I appreciated the blackout curtains since I have trouble sleeping if there’s any light. Also, in spite of being right next to the freeway, there was virtually no noise."

Reviewed on Aug 22, 2025

Holiday Inn Windsor Wine Country by IHG

8755 Old Redwood Hwy, Windsor, CA

Fully refundable

$107 nightly

$122 total

Aug 27 - Aug 28

Total with taxes and fees

9/10 Wonderful! (1,003 reviews)

"Pleasant stay."

Reviewed on Aug 20, 2025

Hampton Inn & Suites Windsor - Sonoma Wine Country

8937 Brooks Road South, Windsor, CA

Fully refundableReserve now, pay when you stay

$144 nightly

$164 total

Aug 31 - Sep 1

Total with taxes and fees

9.2/10 Wonderful! (1,001 reviews)

"Great location in webster, close to all attractions."

Reviewed on Aug 15, 2025

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.

Things to do near Windsor

Windsor, California, is perfect for outdoor and romantic getaways, offering activities like golfing at scenic courses and indulging in body treatments. Visitors can explore local exhibits, enjoy a ski trip at nearby Martock, or embark on a delightful day trip from Windsor. With its beautiful landscapes and charming atmosphere, Windsor promises memorable experiences for all travelers.

Shopping

Windsor offers delightful shopping experiences, including Soda Rock Winery, just 8 miles away, perfect for unique gifts. Santa Rosa Plaza Shopping Center, 9 miles from Windsor, boasts a variety of shops. If you're up for a drive, visit Petaluma Village Premium Outlets, located 22 miles away, for great deals.

Recreation

Experience the vibrant performances at the Luther Burbank Center for the Arts, just 5 miles from Windsor, offering a mix of culture and entertainment for all ages. For outdoor enthusiasts, the Healdsburg Golf Club provides a scenic golf experience, while the Redwood Empire Ice Arena invites you for thrilling ice skating adventures, located 7 miles away.

Adventure

Explore the scenic Bohemian Grove, an 11-mile getaway known for its family-friendly outdoor adventures and natural beauty. For water enthusiasts, Rubicon Adventures, located 8 miles away, offers thrilling water sports. Experience the rush of Sonoma Zipline Adventures, 12 miles from Windsor, with its exciting ropes courses and ziplines.

Nightlife

Windsor's nightlife offers a charming blend of romance and entertainment. Head to the Phoenix Theater, a vibrant nightclub 24 miles away, where you can enjoy city vibes and live performances that create an unforgettable evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Windsor

Windsor, California, is an ideal destination for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can explore popular attractions like the scenic piazzaSquare, the picturesque riverfront, and nearby beaches. The area is rich in culture and offers a vibrant city experience, with highlights including the Windsor Riverfront and the historic Windsor Castle. Whether you're after adventure or relaxation, Windsor has something for everyone.

Russian River: Just 2 miles from Windsor, the Russian River offers stunning scenery and a refreshing outdoor atmosphere. Enjoy activities like kayaking, fishing, or simply relaxing by the riverbanks amidst nature's beauty.
Healdsburg Plaza: Located 5 miles away, Healdsburg Plaza is a vibrant square that showcases local culture and community. Explore charming shops, enjoy delicious dining options, and embrace the lively city vibes that this hub has to offer.
Charles M. Schulz Museum: Situated 7 miles from Windsor, this museum is dedicated to the beloved creator of the Peanuts comic strip. Immerse yourself in the art and history of Schulz’s work while enjoying engaging exhibits that celebrate his legacy.

Best time to go to Windsor

The best time to visit Windsor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windsor falls in July, when visitor numbers are slightly high and weather is sunny with no rain. The coolest average temperature in Windsor falls in December, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	48.2°F (9.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	49.1°F (9.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	51.1°F (10.6°C)	Light Rain	Mostly Sunny	Average	Average
April	55.6°F (13.1°C)	No Rain	Mostly Sunny	Average	Average
May	60.6°F (15.9°C)	No Rain	Sunny	Average	Average
June	67.3°F (19.6°C)	No Rain	Sunny	Slightly High	Average
July	69.8°F (21.0°C)	No Rain	Sunny	Slightly High	Slightly High
August	69.4°F (20.8°C)	No Rain	Sunny	Average	Slightly High
September	68.0°F (20.0°C)	No Rain	Sunny	Average	Slightly High
October	62.1°F (16.7°C)	No Rain	Sunny	Slightly High	Average
November	53.1°F (11.7°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	47.3°F (8.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

Tips to save on your trip to Windsor

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Windsor.
Consider traveling to Windsor during the low season (December to February) for more affordable options.
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.