Windsor Vacations 2025 from CA $996

Windsor flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

RiverPointe Napa Valley Resort

Stonehouse

per person

Jun. 11 - Jun. 14

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Oakland (OAK)

Stay at this 3-star condo in Napa. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Napa Valley Wine Train and Oxbow Public Market are located nearby.

Grand Reserve at The Meritage

Soscol Gateway South

per person

Jun. 11 - Jun. 14

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Oakland (OAK)

Stay at this 4.5-star luxury resort in Napa. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Napa Valley Wine Train and Trinitas Cellars are located nearby.

Silverado Resort

per person

Jun. 11 - Jun. 14

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Oakland (OAK)

Stay at this 4-star spa resort in Napa. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Napa Valley Wine Train and Silverado Resort - North and South Courses are located nearby.

Embassy Suites by Hilton Napa Valley

Central Napa

per person

Jun. 11 - Jun. 14

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Oakland (OAK)

Stay at this resort in Napa. Enjoy free breakfast, room service, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Napa Valley Wine Train and Napa Premium Outlets are located nearby.

Top Windsor hotels deals

Holiday Inn Windsor Wine Country by IHG

8755 Old Redwood Hwy, Windsor, CA

Free cancellation

CA $147

CA $167 total

includes taxes & fees

Apr 20 - Apr 21

Stay at this 3-star business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Russian River and Powell's Sweet Shoppe - Windsor are located nearby.

Pool

Parking included

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

8865 Conde Lane, Windsor, CA

Free cancellation

CA $181

CA $206 total

includes taxes & fees

Apr 6 - Apr 7

Book a stay at this golf hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Russian River and Powell's Sweet Shoppe - Windsor are located nearby.

Pool

Hot tub

Hampton Inn & Suites Windsor - Sonoma Wine Country

8937 Brooks Road South, Windsor, CA

Free cancellation

Reserve now, pay when you stay

CA $193

CA $221 total

includes taxes & fees

Apr 20 - Apr 21

Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Russian River and Powell's Sweet Shoppe - Windsor are located nearby.

Pool

Hot tub

WorldMark Windsor

1251 Shilo Rd, Windsor, CA

Get rates

Stay at this 3-star spa hotel in Windsor. Enjoy free parking, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Russian River and Windsor Golf Club are located nearby.

Pool

Hot tub

The Sandman, Ascend Hotel Collection

3421 Cleveland Ave, Santa Rosa, CA

Free cancellation

Reserve now, pay when you stay

CA $108

CA $125 total

includes taxes & fees

Apr 16 - Apr 17

Stay at this 3-star business-friendly hotel in Santa Rosa. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the bar in our reviews. Popular attractions Charles M. Schulz Museum and Redwood Empire Ice Arena are located nearby.

Pool

Pet-friendly

Flamingo Resort & Spa

2777 4th St, Santa Rosa, CA

Free cancellation

Reserve now, pay when you stay

CA $166

CA $249 total

includes taxes & fees

Apr 27 - Apr 28

Stay at this 4-star spa hotel in Santa Rosa. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sonoma County Fairgrounds and Old Courthouse Square are located nearby.

Pool

Hot tub

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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.

Popular places to visit

Windsor Golf Club

Enjoy a round of golf in Windsor at Windsor Golf Club. Stroll along the area's riverfront, or simply savor its wineries.

Sonoma-Cutrer Vineyards Cutrer Vineyard

You can enjoy a tasting or tour at Sonoma-Cutrer Vineyards Cutrer Vineyard during your travels to Windsor. Attend a sporting event or simply enjoy the wineries while you're in the area.

La Crema Estate at Saralee's Vineyard

You can enjoy a tasting or tour at La Crema Estate at Saralee's Vineyard during your travels to Windsor. Check out the wineries or top-notch restaurants in this family-friendly area.

Windsor Vacations

Even if you're the most impulsive adventurer, it's still good to brush up on one or two things about Windsor before you go. Locate it on your map, figure out the things to do there and let the good times roll!

You'll find this Sonoma Valley neighborhood 20 miles (32 kilometers) northwest of the city center.

Places to visit in Windsor

It doesn't matter whether you're trying to hit a hole-in-one or just in the mood to practice your swing, you're sure to have a blast at Windsor Golf Club. And there's more. Stop counting those calories and don't worry about that monotonous diet. Indulge your passion for a sugary treat at Powell's Sweet Shoppe - Windsor!

Where do you fly into for Windsor?

Landing at Sonoma County Airport (STS)? Windsor is 2 miles (3 kilometers) away. Grab a snack, wave down a cab and you'll be there in no time!

Frequently asked questions

How much are vacation packages to Windsor?

Your vacation dreams can become reality in Windsor for only CA $996. Package deals include flights and hotels, so organizing everything should be a breeze. The only thing you’ll need to concentrate on is having an incredible time.

How long should my Windsor vacation be?

Typically, 2 nights is what many tourists book for their Windsor vacation. That’s a handy guide, but there’s loads more to uncover if you give yourself a couple of extra days.

Where can I get the best vacation package deals for Windsor?

Travelocity has countless ways to score an awesome Windsor package deal. Choose from 400 airlines and 1,000,000 properties across the globe and craft a travel itinerary that’s suited to you. With this amount of choice at your fingertips, it’s time to start booking your next great escape.

Why should I purchase my Windsor vacation bundle via Travelocity?

Travel is all about making cherished new memories and leaving all your troubles behind — which is why we have a team of customer service experts available round-the-clock should you need them. On top of that, our Price Match Guarantee ensures you’ll always get the best price available on our impressive range of vacation packages. So what are you waiting for? There’s no time like the present to lock in the vacation of a lifetime.

Will I save money on my Windsor car rental if I bundle it with my hotel or flight?

Bundling your flight, hotel and car into a Windsor vacation package is a surefire way to land the best prices. Plus, having your own set of wheels gives you total freedom to make your way to all those big sights you can’t wait to check out. Sitting 88 kilometers away from Windsor, Pier 39 is one place that should be on your can’t-miss list. Load up the car and make a day trip of it.

Which airport is best for Windsor?

The best airport is Sonoma County Airport (STS). Grab your bags, step out of the terminal and you’ll find yourself 5 kilometers from central Windsor.

What is there to do in Windsor?

Windsor has more than its fair share of sights to discover, like Windsor Golf Club and Sonoma-Cutrer Vineyards Cutrer Vineyard. These two fantastic attractions are on most visitors’ itineraries.

Where should I stay when visiting Windsor?

If you’re after a place to lay your head, consider the Hampton Inn & Suites Windsor - Sonoma Wine Country. It’s the top choice for many visitors.