Windsor Vacation Packages

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Flight and hotel packages to Windsor

Price found within the past 48 hours. Click for updated prices.
RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort

3 out of 5
Stonehouse
Save 100% on your flight
per person
Jun 28 - Jul 1
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Oakland (OAK)
This condo features an outdoor pool and a gym. Enjoy the spa 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.
Bardessono Hotel and Spa

Bardessono Hotel and Spa

5 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 1
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Silverado Resort

Silverado Resort

4 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 1
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
White House Napa Valley

White House Napa Valley

4 out of 5
Napa Abajo
Save 100% on your flight
per person
Jun 28 - Jul 1
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Oakland (OAK)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. There's an outdoor pool on site, and a terrace and a garden are also provided.
Hotel Yountville

Hotel Yountville

4.5 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 1
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Oakland (OAK)
A full-service spa, 2 spa tubs, and an outdoor pool are all featured at this luxury 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.

Top Windsor hotel deals

Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel

2.5 out of 5
8865 Conde Lane, Windsor, CA
Free Cancellation
The price is $149 per night
$149
per night
May 29 - May 30
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 spa tub and free perks like buffet breakfast and free self parking.
Hot Tub
Breakfast included
Holiday Inn Windsor Wine Country, an IHG Hotel

Holiday Inn Windsor Wine Country, an IHG Hotel

3 out of 5
8755 Old Redwood Hwy, Windsor, CA
Free Cancellation
The price is $161 per night
$161
per night
Jun 23 - Jun 24
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.
Breakfast available
Pool
Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 out of 5
8937 Brooks Road South, Windsor, CA
The price is $169 per night
$169
per night
Jun 23 - Jun 24
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 spa tub and free perks like on-the-go breakfast and free self parking.
Hot Tub
Pet friendly
WorldMark Windsor

WorldMark Windsor

3 out of 5
1251 Shilo Rd, Windsor, CA
Get rates
A full-service spa, 2 outdoor pools, and a spa tub 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.
Hot Tub
Pool
The Sandman Hotel

The Sandman Hotel

3 out of 5
3421 Cleveland Ave, Santa Rosa, CA
Free Cancellation
Reserve now, pay when you stay
The price is $106 per night
$106
per night
May 28 - May 29
This hotel features an outdoor pool and a gym. Business travelers can take advantage of the express check-out. Relax with a drink at the poolside bar and enjoy perks like free self parking.
Pet friendly
Pool
Hyatt Regency Sonoma Wine Country

Hyatt Regency Sonoma Wine Country

4 out of 5
170 Railroad Street, Santa Rosa, CA
Free Cancellation
The price is $161 per night
$161
per night
Jun 2 - Jun 3
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Enjoy the spa tub and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.
Hot Tub
Pet friendly
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See all available properties in Windsor
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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 in Windsor

Image for Windsor Golf Club

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.

Windsor Golf Club
Image for Sonoma-Cutrer Vineyards Cutrer Vineyard

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.

Sonoma-Cutrer Vineyards Cutrer Vineyard
Image for Pacific Coast Air Museum

Pacific Coast Air Museum

You can enjoy some culture when you stop by Pacific Coast Air Museum in Windsor. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Pacific Coast Air Museum

Photos of local treasures

Photo by Jennifer Hill
Photo by Jennifer Hill

Frequently asked questions

How much are vacation packages to Windsor?
Splash out on a fulfilling travel experience in Windsor with a vacation package starting from as low as $533. Organizing your flights, tours and hotels with Travelocity is so simple. What’s more, our deals will leave you with more savings in your pocket for fun times.
How long should my Windsor vacation be?
About 2 nights is what many visitors book for their Windsor trip. That’s an useful guide, but there’s plenty more to discover if you give yourself a little more time.
Where can I get the best vacation package deals for Windsor?
For the best package deal to Windsor, you can’t go past Travelocity. Take your pick from as many as 400 airlines and 1,000,000 properties around the world to create the ultimate adventure — it couldn’t be simpler.
Why should I purchase my Windsor vacation bundle via Travelocity?
Fantastic savings, loads of thrilling destinations and 24/7 customer service you can rely on — that’s why. And with our Price Match Guarantee, you can rest assured knowing that you’ll always score the best possible deal with Travelocity.
Can I save money on my Windsor car rental if I combine it with a hotel or flight?
Combining your flight, hotel and car into a Windsor vacation package is a great way to score better prices. Plus, having your own car rental gives you freedom to find your way to all those big-name sights you’re eager to check out. Situated 55 mi from Windsor, Pier 39 is one attraction that should have a place on your itinerary. Fasten your seat belt and make a day trip of it.
What is the best time of year to go to Windsor?
Take your vacation in and spend more of your money on fun experiences, not your hotel. This is the least costly month to plan your stay. Prices are at their most expensive in , so avoid traveling during this time if you’re eager to save. March, September and October is the peak period in Windsor. You’ll need to book beforehand and be ready to pay higher prices. November, December and January are the quietest months.
Which airport is best for Windsor?
The top airport for Windsor is Sonoma County Airport (STS). It’s located 3 mi north of downtown.
What is there to do in Windsor?
Windsor is full of things to see and do, like Windsor Golf Club and Sonoma-Cutrer Vineyards Cutrer Vineyard. These two popular attractions are on most travelers’ to-do lists.
Where should I stay when visiting Windsor?
Many people stay at the Hampton Inn & Suites Windsor/Sonoma Wine Country. It’s sure to be a great base for your Windsor escape.