Windsor Vacations from $597
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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.
The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
RiverPointe Napa Valley Resort
Stonehouse
Price was $828, price is now $597 per person
$597
per person
Jan 16 - Jan 19
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Oakland (OAK)
8.8/10 Excellent! (1,332 reviews)
clean room, friendly staff, good size resort area. It was cold during my staff so we didn't use the spa or pool. Cottage was smaller than expected, but we enjoyed our stay. Would visit this resort again.
Reviewed on Oct 27, 2025
Claremont Resort & Club
Claremont Hills
Save 100% on your flight
Price was $1,335, price is now $734 per person
$734
per person
Dec 12 - Dec 17
just found
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Oakland (OAK)
8.8/10 Excellent! (1,016 reviews)
Beautiful property! Employees are super kind!
Hope to return!
Reviewed on Nov 1, 2025
DoubleTree by Hilton Hotel Berkeley Marina
Save 100% on your flight
Price was $1,149, price is now $770 per person
$770
per person
Jan 10 - Jan 16
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Oakland (OAK)
8.2/10 Very Good! (3,521 reviews)
Staff was courteous and overall the property was nice. The $40 per night parking fee is outrageous...it is not in downtown SF...plenty of parking spaces available.
Reviewed on Nov 1, 2025
Embassy Suites by Hilton Napa Valley
Central Napa
Save 100% on your flight
Price was $1,220, price is now $822 per person
$822
per person
Jan 10 - Jan 16
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Oakland (OAK)
8.8/10 Excellent! (1,006 reviews)
Paying to park was the only negative
Reviewed on Oct 20, 2025
Carneros Resort and Spa
Save 100% on your flight
Price was $2,176, price is now $1,568 per person
$1,568
per person
Jan 16 - Jan 19
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Oakland (OAK)
9.2/10 Wonderful! (347 reviews)
It is a beautiful property with magnificent grounds. The staff and dining options are great. Highly recommend.
Reviewed on Aug 25, 2025
Discover the most popular places to visit in Windsor
Windsor Golf Club
5/5(2 reviews)
Enjoy a round of golf in Windsor at Windsor Golf Club. Stroll along the area's riverfront, or simply savor its wineries.
Pacific Coast Air Museum
You can spend time studying the exhibits at Pacific Coast Air Museum during your trip to Windsor. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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 top-notch restaurants.
What to do in Windsor
Sebastopol: Guided Wine Tasting Experience with Sommelier
$175
per adult
Santa Rosa North Sonoma County Small Group Winery Tour
$141
per adult
100% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
$139
per adult
96% of travellers recommend
Windsor Hotel Deals
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane, Windsor, CA
Fully refundable
$103 nightly
The price is $117 total per night from Nov 23 to Nov 24
$117 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (1,214 reviews)
The room was quiet, large and clean. What more would anyone want?
Reviewed on Oct 26, 2025
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy, Windsor, CA
Fully refundable
$95 nightly
The price is $108 total per night from Nov 23 to Nov 24
$108 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
Very comfortable hotel with the best staff. The person who checked us in was so nice. The room was spotless and super comfortable
Reviewed on Oct 29, 2025
Hampton Inn & Suites Windsor - Sonoma Wine Country
8937 Brooks Road South, Windsor, CA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $130 total per night from Nov 23 to Nov 24
$130 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
We were in the area for a wedding in Healdsburg and this location was very convenient to the venue. We had a very nice room and all was comfortable. Will stay again.
Reviewed on Oct 30, 2025
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.
Find the Best Windsor Vacation Packages
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Sonoma County Airport (STS) |
Population | 27,500 |
Max Temp Winter | 60ºF |
Max Temp Summer | 80ºF |
Top Sights | Safari West, Francis Ford Coppola Winery and Russian River Vineyard |
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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.