Windsor Vacation Packages 2026 from $627

Windsor flight + hotel vacation packages

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

Silverado Resort

$627

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Oakland (OAK)

A golf course, a full-service spa, and 2 outdoor pools are all featured at this resort. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. Enjoy the 10 outdoor tennis courts and perks like free self parking and free WiFi.

Claremont Resort & Club

Claremont Hills

Save 100% on your flight

$1,120

per person

Apr 12 - Apr 17

found 19 hours ago

Roundtrip flight included

Charlotte (CLT) 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.

Stanly Ranch, Auberge Collection

Save 100% on your flight

$1,404

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Oakland (OAK)

A full-service spa and an outdoor pool are featured at this smoke-free hotel. Enjoy a meal in one of the 2 coffee shops/cafes and free perks like valet parking and WiFi in public areas. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.

Solage, Auberge Collection

Save 100% on your flight

$3,859

per person

Mar 13 - Mar 19

found 20 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Oakland (OAK)

A full-service spa, 6 outdoor pools, and 5 hot tubs are all featured at this smoke-free hotel. Families will appreciate the children's club and complimentary bicycles. Enjoy the gym and perks like free valet parking and free WiFi.

RiverPointe Napa Valley Resort

Stonehouse

Save 100% on your flight

$912

per person

May 6 - May 10

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Oakland (OAK)

This condo features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. There's a sauna on site, and laundry facilities and concierge services are also offered.

Top Windsor hotels deals

Hampton Inn & Suites Windsor - Sonoma Wine Country

8937 Brooks Road South Windsor CA

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$135 total

Feb 22 - Feb 23

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 Express® Windsor Sonoma Wine Country by IHG

8865 Conde Lane Windsor CA

Free Cancellation

$99 nightly

$113 total

Feb 22 - Feb 23

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

Holiday Inn Windsor Wine Country by IHG

8755 Old Redwood Hwy Windsor CA

Free Cancellation

$99 nightly

$113 total

Feb 22 - Feb 23

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 and free WiFi.

Pool

Hot Tub

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$210 nightly

$240 total

Feb 17 - Feb 18

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

$129 nightly

$147 total

Feb 10 - Feb 11

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.

Popular places to visit

Vinery on the hills of Napa Valley, northern California, USA

Russian Hill Estate Vineyards

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 top-notch restaurants while you're in the area.

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 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.

Frequently asked questions

How much are vacation packages to Windsor?

Your vacation dreams can become reality in Windsor for only $627. 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.