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.

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Windsor Hotel Deals

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 $191 per night from Aug 5 to Aug 6
CA $191
CA $218 total
Aug 5 - Aug 6
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"Nice and clean"

Reviewed on Jul 8, 2026

Hampton Inn & Suites Windsor - Sonoma Wine Country
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 $185 per night from Aug 2 to Aug 3
CA $185
CA $210 total
Aug 2 - Aug 3
includes taxes & fees
9.2/10 Wonderful! (1,348 reviews)
"I received a $70 charge for a “stained towel” my son got some Gatorade on a towel. That in no way should be a charge let alone $70! Hoping they will make it right but when I talked to the people at the front desk no manager was on duty and couldn’t help me."

Reviewed on Jul 7, 2026

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
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 $185 per night from Aug 2 to Aug 3
CA $185
CA $210 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (1,063 reviews)
"Nice"

Reviewed on Jul 6, 2026

Holiday Inn Windsor Wine Country by IHG
See all 2,152 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.
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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.
See properties

What to do in Windsor

Shopping in Healdsburg

History Walking Tour of Healdsburg

CA $64
per adult
History Walking Tour of Healdsburg
Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

CA $71
per adult
86% of travellers recommend
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
Healdsburg Wine and Food Pairing Walking Tour

Healdsburg Wine and Food Pairing Guided Walking Tour

CA $197
per adult
96% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
See all activities in Windsor

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices 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.

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