Windsor Vacation Packages 2025/2026 from $521

Windsor flight + hotel vacation packages

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

RiverPointe Napa Valley Resort

Stonehouse

Save 100% on your flight

per person

Oct 3 - Oct 6

found 1 day ago

Roundtrip flight included

Denver (DEN) 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.

River Terrace Inn - A Noble House Hotel

Downtown Napa

per person

Sep 20 - Sep 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Oakland (OAK)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 3 conference rooms, free WiFi in public areas, and laundry service. Free self parking, a terrace, and a garden are also offered.

Silverado Resort

Save 100% on your flight

per person

Sep 20 - Sep 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Hotel Yountville

Save 100% on your flight

per person

Sep 20 - Sep 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Oakland (OAK)

A full-service spa, 2 hot tubs, and an outdoor pool are all featured at this boutique hotel. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.

Claremont Resort & Club

Claremont Hills

Save 100% on your flight

per person

Aug 15 - Aug 18

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Top Windsor hotels deals

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

8865 Conde Lane, Windsor, CA

Free Cancellation

$119 nightly

$136 total

Aug 3 - Aug 4

Total includes 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

$111 nightly

$127 total

Jul 15 - Jul 16

Total includes 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

Hampton Inn & Suites Windsor - Sonoma Wine Country

8937 Brooks Road South, Windsor, CA

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$154 total

Jul 16 - Jul 17

Total includes 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

The Inn at the Tides

800 Coast Hwy One, Bodega Bay, CA

$255 nightly

$291 total

Jul 20 - Jul 21

Total includes taxes and fees

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

Breakfast included

Parking included

Oxford Suites Sonoma County

67 Golf Course Drive W., Rohnert Park, CA

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$158 total

Jul 15 - Jul 16

Total includes taxes and fees

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

Hot Tub

Breakfast included

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

2777 4th St, Santa Rosa, CA

$179 nightly

$207 total

Jul 15 - Jul 16

Total includes taxes and fees

A full-service spa, 2 outdoor pools, and 5 outdoor tennis courts are featured at this smoke-free hotel. Families will appreciate the picnic area, kid-friendly dining, and babysitting. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

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

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 top-notch restaurants.

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 top-notch restaurants or wineries in this family-friendly 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 wineries while you're in the area.

Frequently asked questions

How much are vacation packages to Windsor?

Your vacation dreams can become reality in Windsor for only $521. 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.