Windsor Holidays

Photo by Rick Alvarez
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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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

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

Top hotels in Windsor

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 S$174 per night from 3 Aug to 4 Aug
S$174
3 Aug - 4 Aug
includes taxes & fees
9.2/10 Wonderful! (1,034 reviews)
"Nice rooms great staff"

Reviewed on 9 Jul, 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
The price is S$168 per night from 29 Jul to 30 Jul
S$168
29 Jul - 30 Jul
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Great front desk. Quiet and clean hotel."

Reviewed on 10 Jul, 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
The price is S$199 per night from 27 Jul to 28 Jul
S$199
27 Jul - 28 Jul
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Great property, the rooms were wonderful and the complimentary breakfast was excellent!"

Reviewed on 9 Jul, 2025

Hampton Inn & Suites Windsor - Sonoma Wine Country
See all 2,108 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

Napa Private Tour

Napa Private Tour

S$45
per traveller
Napa Private Tour
Private Professional Vacation Photoshoot in Santa Rosa CA

Private Professional Vacation Photoshoot in Santa Rosa CA

S$267
per adult
Private Professional Vacation Photoshoot in Santa Rosa CA
Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

S$64
per adult
84% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.