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.
Marina Village Inn
Price was CA $898, price is now CA $575 per person
CA $575
per person
Nov 10 - Nov 17
found 24 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
7.2/10 Good! (1,003 reviews)
A lot of good places bars and night life close by. Front staff very helpful. Quiet and easy check in check out process.
Reviewed on Aug. 17, 2025
RiverPointe Napa Valley Resort
Stonehouse
Price was CA $1,226, price is now CA $756 per person
CA $756
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Oakland (OAK)
8.8/10 Excellent! (1,305 reviews)
I always feel like I'm on vacation here. Even if I travel to Napa for work, this is a perfect escape. We love the pool and ping pong area plus the landscape is great, green and quiet.
Reviewed on Aug. 24, 2025
Silverado Resort
Price was CA $3,773, price is now CA $2,382 per person
CA $2,382
per person
Nov 3 - Nov 8
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Oakland (OAK)
8.8/10 Excellent! (1,037 reviews)
I did not like the stacked parking. My car got blocked in by another guests car when I parked.
Reviewed on Aug. 27, 2025
River Terrace Inn - A Noble House Hotel
Downtown Napa
Price was CA $1,984, price is now CA $1,331 per person
CA $1,331
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Oakland (OAK)
9/10 Wonderful! (1,001 reviews)
Very easy to check in with ample parking. Front desk personnel were very friendly. Wine tasting was a added treat. Outside patio was the best.
Reviewed on Aug. 24, 2025
Windsor Hotel Deals
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane, Windsor, CA
Fully refundable
The price is CA $168 per night from Sep 1 to Sep 2
CA $168
CA $191 total
Sep 1 - Sep 2
includes taxes & fees
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy, Windsor, CA
Fully refundable
The price is CA $147 per night from Sep 7 to Sep 8
CA $147
CA $168 total
Sep 7 - Sep 8
includes taxes & fees
Hampton Inn & Suites Windsor - Sonoma Wine Country
8937 Brooks Road South, Windsor, CA
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Sep 28 to Sep 29
CA $192
CA $219 total
Sep 28 - Sep 29
includes taxes & fees
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 wineries.
What to do in Windsor
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
CA $69
per adult
84% of travellers recommend
Self-Guided Audio Driving Tour of Sonoma and Napa Valley
CA $23
per traveller
Healdsburg Wine and Food Pairing Guided Walking Tour
CA $191
per adult
96% of travellers recommend
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Vacation Rentals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.