Windsor Holidays

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Top Flight + Hotel Deals in Windsor

Price found within the past 48 hours. Click for updated prices.
Sonesta Emeryville - San Francisco Bay Bridge

Sonesta Emeryville - San Francisco Bay Bridge

€1,136
per person
19 Sept - 26 Sept
found 1 day ago
Return flight included
Brussels (BRU) to Oakland (OAK)
8.6/10 Excellent! (1,622 reviews)
Claremont Resort & Club

Claremont Resort & Club

Claremont Hills
€1,980
per person
19 Sept - 26 Sept
found 1 day ago
Return flight included
Brussels (BRU) to Oakland (OAK)
9/10 Wonderful! (1,064 reviews)
I love that nothing is plastic or paper. Everything is reusable and the soaps and lotions all smell delicious. I love the plants on the table throughout the hallways.

Reviewed on 15 Aug 2026

DoubleTree by Hilton Hotel Berkeley Marina

DoubleTree by Hilton Hotel Berkeley Marina

Berkeley Marina
€1,256
per person
19 Sept - 26 Sept
found 1 day ago
Return flight included
Brussels (BRU) to Oakland (OAK)
8.2/10 Very good! (5,005 reviews)
Home2 Suites by Hilton Alameda Oakland Airport

Home2 Suites by Hilton Alameda Oakland Airport

Bay Farm Island
€1,627
per person
19 Sept - 26 Sept
found 1 day ago
Return flight included
Brussels (BRU) to Oakland (OAK)
9/10 Wonderful! (572 reviews)
Executive Inn & Suites Embarcadero Cove

Executive Inn & Suites Embarcadero Cove

San Antonio
€1,206
per person
19 Sept - 26 Sept
found 1 day ago
Return flight included
Brussels (BRU) to Oakland (OAK)
9/10 Wonderful! (1,166 reviews)
rooms are a bit old but clean! lobby is renovated and well-maintained

Reviewed on 14 Aug 2026

Top hotels in Windsor

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

8865 Conde Lane Windsor CA
Fully refundable
€114
13 Sept - 14 Sept
includes taxes & fees
9.2/10 Wonderful! (1,332 reviews)
"Staff was great! My sole complaint about our stay was that the bathroom lacked a fan. The room became musty after showers and this triggered my asthma and made it difficult for me to sleep and difficultto relax on a weekendaway, celebrating my birthday. Also, the pool and hot tub were out of order. ..."

Reviewed on 13 Aug 2026

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country

8937 Brooks Road South Windsor CA
Fully refundableReserve now, pay when you stay
€145
24 Aug - 25 Aug
includes taxes & fees
Hampton Inn & Suites Windsor - Sonoma Wine Country
Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG

8755 Old Redwood Hwy Windsor CA
Fully refundable
€129
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,067 reviews)
"Very clean room. Staff went out of their way to assist us."

Reviewed on 10 Aug 2026

Holiday Inn Windsor Wine Country by IHG
See all 2,157 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 savouring their distinctive wines.
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La Crema Estate at Saralee's Vineyard

This historic barn-turned-tasting room showcases La Crema's acclaimed cool-climate wines in Russian River Valley. Savour vineyard views while experiencing guided tastings or speciality pairings.
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Windsor Golf Club

8.8/10 (19 reviews)
This championship course winds through Sonoma wine country, challenging golfers with scenic water hazards and majestic oaks. Enjoy innovative cuisine at Charlie's Restaurant overlooking the countryside.
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Pacific Coast Air Museum

10.0/10 (4 reviews)
The Pacific Coast Air Museum displays meticulously preserved aircraft spanning decades of aviation history. Climb into cockpits during "Open Cockpit Day" events for a pilot's perspective.
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Windsor Oaks Vineyards

9.6/10 (5 reviews)
This estate produces premium wines across three appellations, with various grapes thriving in diverse microclimates. Visit during exclusive open days to savour handcrafted wines amid preserved natural beauty.
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Dom Whitney Tasting Lounge

8.6/10 (4 reviews)
This Windsor wine sanctuary showcases multiple local wineries under one welcoming roof. Knowledgeable staff guide you through diverse regional varietals while sharing insights about Sonoma's winemaking heritage.
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Martinelli Vineyard

8.6/10 (4 reviews)
Housed in a historic hop barn, Martinelli Winery showcases five generations of family winemaking expertise. Sample their estate-grown Pinot Noir and Zinfandel while learning about 135 years of viticultural heritage.
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Powell's Sweet Shoppe - Windsor

10.0/10 (7 reviews)
Powell's Sweet Shoppe transported visitors to a sweets wonderland with nostalgic treats and vintage toys. The shop's continuous playing of "Charlie and the Chocolate Factory" created a whimsical atmosphere for all ages.
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What to do in Windsor

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

€44
per adult
86% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Shopping in Healdsburg

History Walking Tour of Healdsburg

€39
per adult
History Walking Tour of Healdsburg
Full Day Guided Electric Bike Wine Tasting Tour with Lunch

Full Day Guided Electric Bike Wine Tasting Tour with Lunch

€174
per adult
Full Day Guided Electric Bike Wine Tasting Tour with Lunch
See all activities in Windsor

Frequently asked questions

How much does a Windsor holiday package cost?
Offering great value package deals from €1,136 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.

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