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.
Claremont Resort & Club
Claremont Hills
CA $2,260
per person
Sep 28 - Oct 2
found 23 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Oakland (OAK)
9/10 Wonderful! (1,064 reviews)
A bottle of fine champagne and chocolates for our anniversary greeted us in our cozy room!
Reviewed on Aug 21, 2026
Lavender, A Four Sisters Inn
CA $2,284
per person
Sep 27 - Sep 30
found 24 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.8/10 Excellent! (448 reviews)
I would definitely stay here again. They were very helpful and attentive but not in the way. It's a very quiet place just off the main road that runs through town. I loved sitting on the porch in the mornings and drinking my coffee. Close to everything we wanted to see in the valley.
Reviewed on Aug 10, 2026
Brannan Cottage Inn
CA $1,343
per person
Nov 1 - Nov 6
found 14 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
9.6/10 Exceptional! (171 reviews)
Hidden gem! Fireplace king rooms are superb. Location is 5/5, walking distance whether you desire wine tasting, mud baths exploring nature or Calistoga’s fine cuisine . Nicole and overall staff just went above and beyond to make this an exceptional experience for an anniversary celebration. Will be back soon!
Reviewed on Aug 16, 2026
Ready to book your vacation to Windsor?
Windsor Hotel Deals
Hampton Inn & Suites Windsor - Sonoma Wine Country
8937 Brooks Road South Windsor CA
Fully refundableReserve now, pay when you stay
CA $196
CA $224 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"Staff is always accommodating. The area is ideally situated for area travel."
Reviewed on Aug 21, 2026
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane Windsor CA
Fully refundable
CA $164
CA $187 total
Sep 20 - Sep 21
includes taxes & fees
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy Windsor CA
Fully refundable
CA $181
CA $206 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (1,069 reviews)
"The kitchen staff was wonderful. We really enjoyed the fresh made breakfast. Thank you"
Reviewed on Aug 22, 2026
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.
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.
Windsor Golf Club
8.8/10 (19 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 wineries or top-notch restaurants in this family-friendly area.
Pacific Coast Air Museum
10.0/10 (4 reviews)
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 Oaks Vineyards
9.6/10 (5 reviews)
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.
Dom Whitney Tasting Lounge
8.6/10 (4 reviews)
Enjoy an outing to Dom Whitney Tasting Lounge during your stay in Windsor. Wander the area's riverfront or simply enjoy one of its wineries.
Powell's Sweet Shoppe - Windsor
10.0/10 (7 reviews)
Enjoy an outing to Powell's Sweet Shoppe - Windsor during your stay in Windsor. Stroll along the area's riverfront, or simply savor its top-notch restaurants.
Martinelli Vineyard
8.6/10 (4 reviews)
You can enjoy a tasting or tour at Martinelli Vineyard during your travels to Windsor. Attend a sporting event or simply enjoy the wineries while you're in the area.
What to do in Windsor
Calaveras Wine Tour - Self-Guided Audio Experience
CA $42
per traveller
Icon Wine & Food Pairing at Williamson Wines in Healdsburg
CA $70
per adult
86% of travellers recommend
Frequently asked questions
How much does a Windsor vacation package cost?
You'll find cheap prices from CA $919 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?
- 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.
- 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.
- 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.
- 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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- Visit Windsor
- River Rock Casino
- Sonoma County Vacations
- Yountville Vacations
- San Francisco Vacations
- Sonoma Vacations
- Charles Krug Winery
- Armstrong Redwoods State Park
- Sharpsteen Museum
- Chateau Montelena Winery
- Sonoma Coast State Park
- Ledson Winery and Vineyards
- V. Sattui Winery
- Santa Rosa Vacations
- Occidental Vacations
- Napa Valley Balloons
- Osmosis Day Spa Sanctuary
- Golden Gate Bridge
- Windsor Oaks Vineyards
- Castello di Amorosa
- Robert Mondavi Winery
- St. Helena Vacations
- Doran Beach
- Dry Creek Vineyard
- Petaluma Vacations
- Alcatraz Island
- Calistoga Hot Springs
- Calistoga Vacations
- Bohemian Grove
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
