Windsor Vacations from $439

Book a Hotel + Flight or Car together to unlock savings

Photo by Rick Alvarez
  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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
River Terrace Inn - A Noble House Hotel
Claremont Resort & Club
Calistoga Wine Ranch
Geyserville Inn
Don't see what you're looking for?
See all available trips from Columbus to Windsor
View all trips

Discover the most popular places to visit in Windsor

What to do in Windsor

Windsor Hotel Deals

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
$119 nightly
The price is $136 total per night from Aug 3 to Aug 4
$136 total
Aug 3 - Aug 4
Total includes taxes and fees
9.2/10 Wonderful! (1,025 reviews)
"Nice room and stay"

Reviewed on Jul 6, 2025

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
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
$107 nightly
The price is $122 total per night from Jul 13 to Jul 14
$122 total
Jul 13 - Jul 14
Total includes taxes and fees
9/10 Wonderful! (1,001 reviews)
"Staff was very friendly"

Reviewed on Jul 7, 2025

Holiday Inn Windsor 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
$135 nightly
The price is $154 total per night from Jul 16 to Jul 17
$154 total
Jul 16 - Jul 17
Total includes taxes and fees
9.2/10 Wonderful! (1,004 reviews)
"Everything we needed and expected in this family friendly, budget friendly hotel. No complaints."

Reviewed on Jul 6, 2025

Hampton Inn & Suites Windsor - Sonoma Wine Country
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.

Find the Best Windsor Vacation Packages

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sonoma County Airport (STS)
Population
27,500
Max Temp Winter
60ºF
Max Temp Summer
80ºF
Top Sights
Safari West, Francis Ford Coppola Winery and Russian River Vineyard

More vacations you might like

Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $439 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?

  1. Pick your travel dates: What you'd like to do in Windsor and your preferred season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.
  5. Bundle your accommodations and airfare: After you've nailed down your trip dates and duration, book the right Windsor vacation package for you.
  6. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.