Windsor Trips (flight + hotel)

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Top hotels in Windsor

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 P8,275 per night from Aug 2 to Aug 3
P8,275
P9,450 total
Aug 2 - Aug 3
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Nice room, bed comfortable, quiet."

Reviewed on Jul 12, 2026

Hampton Inn & Suites Windsor - Sonoma Wine Country
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
The price is P7,006 per night from Aug 9 to Aug 10
P7,006
P7,987 total
Aug 9 - Aug 10
includes taxes & fees
9.2/10 Wonderful! (1,351 reviews)
"Staff was very nice and helpful.Room was very clean and the breakfast was good."

Reviewed on Jul 12, 2026

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 P7,294 per night from Aug 10 to Aug 11
P7,294
P8,315 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,064 reviews)
"Nice"

Reviewed on Jul 6, 2026

Holiday Inn Windsor Wine Country by IHG
See all 2,172 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.

Stay near popular Windsor attractions

Russian Hill Estate Vineyards

9.6/10 (4 reviews)
Russian Hill Estate crafted acclaimed Pinot Noir and Syrah from Sonoma's Russian River Valley terroir. Visitors enjoyed intimate tastings with vineyard views and picnic areas perfect for savoring their distinctive wines.
See properties

What to do in Windsor

Shopping in Healdsburg

History Walking Tour of Healdsburg

P2,736
per adult
History Walking Tour of Healdsburg
Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

P3,040
per adult
86% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Sebastopol: Guided Wine Tasting Experience with Sommelier

Sebastopol: Guided Wine Tasting Experience with Sommelier

P10,639
per adult
Sebastopol: Guided Wine Tasting Experience with Sommelier
See all activities in Windsor

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.

Explore a world of travel with Expedia

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