Windsor Vacation Packages

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Your Windsor Vacation

Uncover the best parts of Windsor with a customized Windsor vacation package. From its lively atmosphere and cultural experiences to its spectacular views, you'll love experiencing this picturesque city the way you want to. Like to start exploring your surroundings? Windsor Golf Club, Sonoma-Cutrer Vineyards Cutrer Vineyard and Windsor Oaks Vineyards are three of the top places to visit during a trip to Windsor. Browse Expedia's wide range of travel options and start planning your ideal vacation to Windsor now.

Top Windsor Vacation Deals

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

RiverPointe Napa Valley Resort

3 out of 5
Stonehouse
per person
Sep 10 - Sep 14
found 20 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.6/10 Excellent! (1,281 reviews)
Cute and cozy cabin. Nice pool and hot tub

Reviewed on Aug. 1, 2025

Silverado Resort

Silverado Resort

4 out of 5
per person
Oct 1 - Oct 5
found 20 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.8/10 Excellent! (1,013 reviews)
Fabulous property and location. We would stay here again. They do allow pets in some areas and we happened to get a unit by a barky dog.

Reviewed on Jul. 29, 2025

Vino Bello Resort

Vino Bello Resort

4 out of 5
Soscol Gateway South
per person
Sep 10 - Sep 14
found 20 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.4/10 Very Good! (1,001 reviews)
Beautiful property. Spacious and clean.

Reviewed on Jul. 28, 2025

Claremont Resort & Club

Claremont Resort & Club

5 out of 5
Claremont Hills
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.8/10 Excellent! (1,010 reviews)
The staff was remarkable. Best service in an American hotel in 20 years. Pool area relaxing and wonderful. Mens locker area with jacuzzi, steam and sauna - top notch.

Reviewed on Jul. 25, 2025

White House Napa Valley

White House Napa Valley

4 out of 5
Napa Abajo
per person
Sep 26 - Sep 30
found 19 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
9.2/10 Wonderful! (596 reviews)
A unique Victorian place that had undergone modern remodel. Quiet and charming!

Reviewed on Jun. 27, 2025

Ready to book your vacation to Windsor?

 

Choose your dates

Windsor Hotel Deals

Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG

3 out of 5
8755 Old Redwood Hwy, Windsor, CA
Fully refundable
The price is CA $148 per night from Aug 3 to Aug 4
CA $148
CA $169 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"New clean convient"

Reviewed on Jul. 30, 2025

Holiday Inn Windsor Wine Country by IHG
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

2.5 out of 5
8865 Conde Lane, Windsor, CA
Fully refundable
The price is CA $165 per night from Aug 3 to Aug 4
CA $165
CA $188 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (1,083 reviews)
"Vehicle was gated in and safe."

Reviewed on Jul. 29, 2025

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
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
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from Aug 20 to Aug 21
CA $182
CA $207 total
Aug 20 - Aug 21
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Very clean! Extremely friendly staff."

Reviewed on Jul. 30, 2025

Hampton Inn & Suites Windsor - Sonoma Wine Country
See all 2,107 properties in Windsor
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Discover the most popular places to visit in Windsor

Windsor Oaks Vineyards

You can enjoy a tasting or tour at Windsor Oaks Vineyards during your travels to Windsor. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Windsor Oaks Vineyards

What to do in Windsor

Self Guided Audio Driving Tour from Vancouver to Whistler

Self-Guided Audio Driving Tour of Sonoma and Napa Valley

CA $23
per traveller
Self-Guided Audio Driving Tour of Sonoma and Napa Valley
Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

CA $69
per adult
84% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Giant Redwoods Tour Including a 4-Course Winery Lunch

Giant Redwoods Tour Including a 5-Course Winery Lunch

CA $321
per adult
100% of travellers recommend
Giant Redwoods Tour Including a 5-Course Winery Lunch
See all activities in Windsor

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from CA $753 on Expedia for your Windsor getaway. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
If you're looking to snag a cheap Windsor vacation package, consider travelling in December, January and February. You'll typically find lower prices on hotels and airfares during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Windsor?
The ideal length of your Windsor vacation depends on what you'd like to see. Generally, a few days to a week will give you time to go to all the top attractions and discover some hidden treasures along the way.
Is it worth booking a vacation package to Windsor?
It's no wonder a Windsor vacation is on the to-do list of many travellers. Top attractions like Windsor Golf Club are just the start of what you can explore here.
How to find the best Windsor package deals?
Bagging a cheap Windsor package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most wallet-friendly Windsor package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your Windsor break by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse the best flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Windsor?
If you've got your Windsor vacation dates confirmed, book early to score some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Windsor?

  1. Choose when to get away: Check your diary and get your bags packed. Your favourite season and the type of activities available will also help you decide when to escape to Windsor.
  2. Plan your budget wisely: As well as the cost of your hotel, you should consider other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Windsor.
  3. Decide your trip length: Consider how much time you want to spend exploring Windsor. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Windsor vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.