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.
Hotel Yountville
Price was CA $2,098, price is now CA $1,488 per person
CA $1,488
per person
Jun 11 - Jun 14
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to Oakland (OAK)
9.6/10 Exceptional! (1,003 reviews)
Everything was fantastic great location great food great vibe lots of very nice things on the property. However, there is no door on the bathroom. That’s our only knock.
Reviewed on Apr 1, 2026
Vino Bello Resort
Soscol Gateway South
Price was CA $2,076, price is now CA $1,492 per person
CA $1,492
per person
Jun 11 - Jun 14
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to Oakland (OAK)
8.4/10 Very Good! (1,001 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 $4,395, price is now CA $3,163 per person
CA $3,163
per person
Jun 11 - Jun 14
found 15 hours ago
Roundtrip flight included
Montreal (YUL) 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 $170 per night from May 3 to May 4
CA $170
CA $194 total
May 3 - May 4
includes taxes & fees
9/10 Wonderful! (1,053 reviews)
Clean room but understaffed.
Reviewed on Apr 2, 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 $200 per night from Apr 20 to Apr 21
CA $200
CA $228 total
Apr 20 - Apr 21
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
While I understand the breakfast buffet was temporarily moved due to renovations, the overall experience was disappointing: the waffles—typically a highlight—were inconsistent (runny one day, overly thick the next), the food area was not kept clean, tables were left unbussed with debris from previous ...
Reviewed on Apr 7, 2026
WorldMark Windsor
1251 Shilo Rd Windsor CA
9/10 Wonderful! (381 reviews)
Super clean. Fun. Kids loved it.
Reviewed on Apr 7, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
