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.
Sonesta Emeryville - San Francisco Bay Bridge
Price was CA $1,081, price is now CA $833 per person
CA $833
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Oakland (OAK)
8.6/10 Excellent! (1,395 reviews)
Room not cleaned well, had lots of hair in the bathroom. Staff were good. Did not have breakfast. Parking was safe but not easy.
Reviewed on Apr 12, 2026
Claremont Resort & Club
Claremont Hills
Price was CA $2,400, price is now CA $1,501 per person
CA $1,501
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Oakland (OAK)
9/10 Wonderful! (1,009 reviews)
Space was clean, only two staff members were nice to me.
Reviewed on Apr 11, 2026
The Meritage Resort and Spa
Soscol Gateway South
Price was CA $4,069, price is now CA $3,009 per person
CA $3,009
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Oakland (OAK)
8.2/10 Very Good! (1,002 reviews)
Not ce property and courteous stafd
Reviewed on Apr 10, 2026
Vino Bello Resort
Soscol Gateway South
Price was CA $3,259, price is now CA $2,484 per person
CA $2,484
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Oakland (OAK)
8.4/10 Very Good! (1,000 reviews)
not exposed or told of spa. room = no utensils. surprised by sales pitch upon checking in.
Reviewed on Mar 22, 2026
Carneros Resort and Spa
Price was CA $3,842, price is now CA $2,967 per person
CA $2,967
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
9.2/10 Wonderful! (363 reviews)
Carneros is located perfectly to travel around the Napa valley but you don't have to leave the property because it has everything you need. My wife and I loved our stay.
Reviewed on Mar 17, 2026
Windsor Hotel Deals
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy Windsor CA
Fully refundable
The price is CA $163 per night from May 10 to May 11
CA $163
CA $186 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (1,056 reviews)
Roy at the reception desk greeted us & was very patient with me (I'm old & was tired from the travel). He smiled a lot & was very helpful. The room was neat and clean. I LOVED the bed and slept very well. Breakfast the next morning was pleasant. There was a buffet, but Jovani the cook made fresh ...
Reviewed on Apr 11, 2026
Hampton Inn & Suites Windsor - Sonoma Wine Country
8937 Brooks Road South Windsor CA
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from Apr 28 to Apr 29
CA $195
CA $223 total
Apr 28 - Apr 29
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
Clean room
Reviewed on Apr 11, 2026
WorldMark Windsor
1251 Shilo Rd Windsor CA
9/10 Wonderful! (383 reviews)
The property is good and these are individually owned apartments. Few things unique to this property to notice. AC would stop when there is no movement within the property. The goal is to save on energy, which I get, but when someone goes to sleep, since there is no one moving, the ac stops. I had ...
Reviewed on Apr 8, 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 wineries.
What to do in Windsor
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
CA $68
per adult
86% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
CA $190
per adult
96% of travellers recommend
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- Windsor Oaks Vineyards
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
