Windsor Vacations

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 ₩234,741 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

Find the Best Windsor Vacation Packages

Windsor Hotel Deals

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
The price is ₩148,192 per night from Aug 10 to Aug 11
₩148,192
₩168,939 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Nice- clean"

Reviewed on Aug 5, 2025

Holiday Inn Windsor Wine Country by IHG
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
The price is ₩168,966 per night from Sep 4 to Sep 5
₩168,966
₩192,621 total
Sep 4 - Sep 5
includes taxes & fees
9.2/10 Wonderful! (1,099 reviews)
"The front desk attendant Matt was very helpful and nice!"

Reviewed on Aug 5, 2025

Holiday Inn Express® Windsor Sonoma 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
The price is ₩181,293 per night from Aug 20 to Aug 21
₩181,293
₩207,034 total
Aug 20 - Aug 21
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"Very clean! Extremely friendly staff."

Reviewed on Jul 30, 2025

Hampton Inn & Suites Windsor - Sonoma Wine Country
See all 2,111 properties in Windsor
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.

Discover the most popular places to visit in Windsor

Dom Whitney Tasting Lounge

Enjoy an outing to Dom Whitney Tasting Lounge during your stay in Windsor. Wander the area's riverfront or simply enjoy one of its wineries.

Dom Whitney Tasting Lounge

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.