Windsor Holidays

Photo by Rick Alvarez

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Top hotels in Windsor

Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG

3 out of 5
8755 Old Redwood Hwy, Windsor, CA
The price is €97 per night from 27 Aug to 28 Aug
€97
27 Aug - 28 Aug
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
Confortable and Convenient for Family
"Confortable and convenient for our Yarn Crawl in Wine Country. Enjoyed being able to walk to eating places."

Reviewed on 14 Aug 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 €116 per night from 24 Aug to 25 Aug
€116
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (1,133 reviews)
"Very nice property and clean"

Reviewed on 20 Aug 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
The price is €128 per night from 26 Aug to 27 Aug
€128
26 Aug - 27 Aug
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Great location in webster, close to all attractions."

Reviewed on 15 Aug 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.

What to do in Windsor

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

€43
per adult
84% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Self Guided Audio Driving Tour from Vancouver to Whistler

Self-Guided Audio Driving Tour of Sonoma and Napa Valley

€15
per traveller
Self-Guided Audio Driving Tour of Sonoma and Napa Valley
Healdsburg Wine and Food Pairing Walking Tour

Healdsburg Wine and Food Pairing Guided Walking Tour

€120
per adult
96% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
See all activities in Windsor

Frequently asked questions

How much does a Windsor holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday 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 holiday package, consider visiting in December, January and February. You'll typically find better rates on accommodation and flights during these months — perfect for travellers wishing to save money.
How many days is enough for Windsor?
The ideal length of your Windsor holiday 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 holiday package to Windsor?
Windsor is a good holiday 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 holiday 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 holiday package as early as possible.
Is it cheaper to book a Windsor holiday as a package?
You can enjoy significant savings on your next Windsor getaway by booking a personalised holiday 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 holiday package to Windsor?
If you have your Windsor holiday 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 travelling 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 accommodation, 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 accommodation and airfare: Once you've settled on your dates and duration, book the ideal Windsor holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.