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.
Claremont Resort & Club
Claremont Hills
Price was CA $1,440, price is now CA $1,024 per person
CA $1,024
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
9/10 Wonderful! (1,003 reviews)
Parking was difficult with automation. Difficult getting out. Need a gate person. Gate automated bar almost hit my hood. Valets were on their phones not helpful. Would consider not staying thete until they fix it. A five star hotel needs 5 star personnel. Not more automation
Reviewed on May 18, 2026
Hotel Yountville
Price was CA $2,618, price is now CA $1,828 per person
CA $1,828
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
9.6/10 Exceptional! (1,006 reviews)
We had a wonderful two night stay and wished we had more time. The room was magnificent, huge with soaking tub, shower, Nespresso machine,… The resort has all you could want, pool, hot tub, spa,… The Yountville location is perfect for walking to a bunch of top restaurants.
Reviewed on May 23, 2026
the cottages of napa valley
Price was CA $2,085, price is now CA $1,510 per person
CA $1,510
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
10/10 Exceptional! (19 reviews)
Beautiful cottage and amenities. LOVED the morning delivery of baked goods, and the jacuzzi tub. Truly the best romantic getaway in Napa.
Reviewed on Apr 12, 2026
RiverPointe Napa Valley Resort
Stonehouse
Price was CA $1,401, price is now CA $1,036 per person
CA $1,036
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.8/10 Excellent! (1,375 reviews)
Nice enough for a short stay. 20 min walk to downtown. Bed was a little squeaky and not the most comfortable but it was clean and easy
Reviewed on May 17, 2026
Windsor Hotel Deals
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy Windsor CA
Fully refundable
The price is CA $175 per night from Jun 22 to Jun 23
CA $175
CA $200 total
Jun 22 - Jun 23
includes taxes & fees
9/10 Wonderful! (1,066 reviews)
"NO breakfast Parking was plenty and safe"
Reviewed on May 19, 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 $191 per night from Jun 7 to Jun 8
CA $191
CA $219 total
Jun 7 - Jun 8
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Love the location and pool"
Reviewed on May 21, 2026
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane Windsor CA
Fully refundable
The price is CA $169 per night from Jun 21 to Jun 22
CA $169
CA $192 total
Jun 21 - Jun 22
includes taxes & fees
9.2/10 Wonderful! (1,351 reviews)
"Very friendly staff. Convenient location, and nice complimentary toiletries."
Reviewed on May 22, 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.
