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.
DoubleTree by Hilton Hotel Berkeley Marina
Berkeley Marina
Price was CA $1,020, price is now CA $756 per person
CA $756
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Oakland (OAK)
8.2/10 Very good! (4,838 reviews)
Pillows is horrible woke up with a sore neck and the balcony’s need some cleaning and wipe down
Reviewed on Jul 12, 2026
Claremont Resort & Club
Claremont Hills
Price was CA $2,364, price is now CA $1,587 per person
CA $1,587
per person
Oct 3 - Oct 8
found 9 hours ago
Roundtrip flight included
Edmonton (YEG) to Oakland (OAK)
9/10 Wonderful! (1,028 reviews)
Parking is a bit pricey and it would be nice if there was at least a discount for overnight guests. Appreciate that there are plenty of water fountains to fill your own bottle with filtered water. Room was clean and very pretty, bathroom was humongous. Pool area was well maintained but there were not enough sun chairs for everyone on Saturday afternoon. This is the perfect little resort to come for a whole family wellness trip to swim, exercise and eat well.
Reviewed on Jul 11, 2026
The Setting Inn Napa Valley
Price was CA $2,309, price is now CA $1,686 per person
CA $1,686
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Oakland (OAK)
10/10 Exceptional! (326 reviews)
Amazing place, quiet, clean and so convient to Napa wineries and restaurants! 100% come back again!
Reviewed on Jun 28, 2026
Home2 Suites by Hilton Alameda Oakland Airport
Bay Farm Island
Price was CA $1,444, price is now CA $1,087 per person
CA $1,087
per person
Sep 23 - Sep 28
found 2 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Oakland (OAK)
9/10 Wonderful! (544 reviews)
Great staff and cleaning.
Reviewed on Jul 7, 2026
The Marina Inn on San Francisco Bay
Price was CA $1,404, price is now CA $1,067 per person
CA $1,067
per person
Sep 25 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Oakland (OAK)
8.6/10 Excellent! (2,542 reviews)
our stay was good it was nice for a quick over night resting area the rooms were nice
Reviewed on Jul 11, 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 $190 per night from Aug 3 to Aug 4
CA $190
CA $217 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"Room was good. Dryer was out.. and very limited staff"
Reviewed on Jul 11, 2026
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane Windsor CA
Fully refundable
The price is CA $161 per night from Aug 9 to Aug 10
CA $161
CA $184 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 Windsor Wine Country by IHG
8755 Old Redwood Hwy Windsor CA
Fully refundable
The price is CA $168 per night from Aug 10 to Aug 11
CA $168
CA $191 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,064 reviews)
"Nice"
Reviewed on Jul 6, 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.
Stay near popular Windsor attractions
What to do in Windsor
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
CA $71
per adult
86% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
CA $197
per adult
96% of travellers recommend
Frequently asked questions
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- Visit Windsor
- River Rock Casino
- Sonoma County Vacations
- Yountville Vacations
- San Francisco Vacations
- Sonoma Vacations
- Charles Krug Winery
- Armstrong Redwoods State Park
- Sharpsteen Museum
- Chateau Montelena Winery
- Sonoma Coast State Park
- Ledson Winery and Vineyards
- V. Sattui Winery
- Santa Rosa Vacations
- Occidental Vacations
- Napa Valley Balloons
- Osmosis Day Spa Sanctuary
- Golden Gate Bridge
- Windsor Oaks Vineyards
- Castello di Amorosa
- Robert Mondavi Winery
- St. Helena Vacations
- Doran Beach
- Dry Creek Vineyard
- Petaluma Vacations
- Alcatraz Island
- Calistoga Hot Springs
- Calistoga Vacations
- Bohemian Grove
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
