Windsor Vacation Packages
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Your Windsor Vacation
Uncover the best parts of Windsor with a customized Windsor vacation package. From its lively atmosphere and cultural experiences to its spectacular views, you'll love experiencing this picturesque city the way you want to. Like to start exploring your surroundings? Windsor Golf Club, Sonoma-Cutrer Vineyards Cutrer Vineyard and Windsor Oaks Vineyards are three of the top places to visit during a trip to Windsor. Browse Expedia's wide range of travel options and start planning your ideal vacation to Windsor now.
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Silverado Resort
Price was CA $1,694, price is now CA $1,255 per person
CA $1,255
per person
Mar 16 - Mar 20
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
8.8/10 Excellent! (1,053 reviews)
The room was clean. The clock beside the bed was not set to the correct time and we could not figure out how to change it. I wish the coffee amenities were a better- creamer rather than powdered "stuff"? Our room had no view to speak of, as we overlooked the parking garage. Assessment for 2 days of "Resort" fees, when we are on property for less than 48 hours seemed superfluous.
Reviewed on Feb 6, 2026
Calistoga Motor Lodge and Spa
Price was CA $2,085, price is now CA $1,589 per person
CA $1,589
per person
Mar 16 - Mar 20
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
8.6/10 Excellent! (305 reviews)
It was a charming, well-curated property. They did a great job transforming a motel into a cute, modern version. It would be even better if the front-side rooms had pendant lighting or window shutters to add a bit more character.
The room was clean and comfortable. If I had to mention one downside, it would be the water pressure, which could be improved.
Reviewed on Feb 6, 2026
Windsor Hotel Deals
Hampton Inn & Suites Windsor - Sonoma Wine Country
8937 Brooks Road South Windsor CA
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Feb 22 to Feb 23
CA $161
CA $184 total
Feb 22 - Feb 23
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Clean and courteous
Reviewed on Feb 3, 2026
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane Windsor CA
Fully refundable
The price is CA $135 per night from Feb 22 to Feb 23
CA $135
CA $154 total
Feb 22 - Feb 23
includes taxes & fees
9.2/10 Wonderful! (1,301 reviews)
Staff was very helpful Room was clean
Reviewed on Jan 25, 2026
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy Windsor CA
Fully refundable
The price is CA $135 per night from Mar 1 to Mar 2
CA $135
CA $154 total
Mar 1 - Mar 2
includes taxes & fees
9/10 Wonderful! (1,037 reviews)
Excellent stay—smooth check-in, friendly staff, and a clean, spacious room. Would’ve loved to stay longer.
Reviewed on Feb 1, 2026
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
Windsor Oaks Vineyards
You can enjoy a tasting or tour at Windsor Oaks Vineyards during your travels to Windsor. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.
What to do in Windsor
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
CA $69
per adult
86% of travellers recommend
Self-Guided Audio Driving Tour of Sonoma and Napa Valley
CA $24
per traveller
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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.
