Windsor Vacation Packages 2026 from $589

Windsor flight + hotel vacation packages

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

Claremont Resort & Club

Claremont Hills

Save 100% on your flight

$589

per person

Sep 21 - Sep 24

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Oakland (OAK)

This luxury hotel features 3 restaurants, 3 outdoor pools, and 8 outdoor tennis courts. Bring the family and enjoy the children's club, playground, and kid-friendly dining. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking.

Hennessey Estate

Central Napa

Save 100% on your flight

$1,600

per person

Sep 23 - Sep 27

found 2 days ago

Roundtrip non-stop flight included

Dallas (DFW) to Oakland (OAK)

This bed & breakfast features an outdoor pool and a hot tub. Enjoy the sauna and free perks like local cuisine breakfast and free self parking. Free WiFi in public areas, a communal living room, and express check-out are also on offer.

Lavender, A Four Sisters Inn

Save 100% on your flight

$1,629

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Oakland (OAK)

This bed & breakfast doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A terrace, a garden, and a lobby fireplace are also on offer.

Bardessono Hotel and Spa

Save 100% on your flight

$3,317

per person

Oct 15 - Oct 18

found 15 hours ago

Roundtrip flight included

Denver (DEN) to Oakland (OAK)

A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury resort. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. Enjoy the gym and visit the 2 bars/lounges and poolside bar for drinks.

Top Windsor hotels deals

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

8865 Conde Lane Windsor CA

Free Cancellation

$118 nightly

$135 total

Sep 13 - Sep 14

Total with taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Hampton Inn & Suites Windsor - Sonoma Wine Country

8937 Brooks Road South Windsor CA

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$168 total

Aug 19 - Aug 20

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like on-the-go breakfast and free self parking.

Pool

Hot Tub

Holiday Inn Windsor Wine Country by IHG

8755 Old Redwood Hwy Windsor CA

Free Cancellation

$131 nightly

$149 total

Aug 31 - Sep 1

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Pool

Parking included

WorldMark Windsor

1251 Shilo Rd Windsor CA

Get rates

A full-service spa, 2 outdoor pools, and 4 hot tubs are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$237 nightly

$271 total

Aug 16 - Aug 17

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.

Pool

Hot Tub

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$170 total

Aug 16 - Aug 17

Total with taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like local cuisine breakfast and free self parking.

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.

Stay near popular Windsor attractions

Russian Hill Estate Vineyards

9.6/10 (4 reviews)

You can enjoy a tasting or tour at Russian Hill Estate Vineyards during your travels to Windsor. Attend a sporting event or simply enjoy the wineries while you're in the area.

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Frequently asked questions

How much are vacation packages to Windsor?

Your vacation dreams can become reality in Windsor for only $589. 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 55 mi 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 3 mi 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.