Windsor Vacations from $392

Book a Hotel + Flight or Car together to unlock savings

Photo by Jennifer Hill
Choose one or more items to build your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Windsor Vacation

From its lively atmosphere to its spectacular views and cultural experiences, you'll find a bunch of great reasons to spend some time in the charming city of Windsor. Experience these highlights and more when you lock in your vacation package to Windsor. If taking in sights is part of the program during your trip to Windsor, look around major attractions like Kendall-Jackson Wine Estate and Gardens, Healdsburg Plaza and Luther Burbank Center for the Arts. Expedia has what you need to escape your daily routine. Tailor your vacation to Windsor to suit your travel style, whatever that may look like.

The Latest Windsor Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott Oakland Downtown

Residence Inn by Marriott Oakland Downtown

3.5 out of 5
Downtown Oakland
per person
Aug 31 - Sep 5
found 2 hours ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
9.2/10 Wonderful! (91 reviews)
Great stay! Everything you need and more for a great value. Laundry, big room, excellent space to work. Fridge is great! Would very happily stay again

Reviewed on Jun 21, 2024

Claremont Club & Spa - A Fairmont Hotel

Claremont Club & Spa - A Fairmont Hotel

5 out of 5
Claremont Hills
per person
Aug 2 - Aug 4
found 1 hour ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
8.8/10 Excellent! (1,002 reviews)
Beautiful location and facilities (the pool and club are wonderful). However not all spa facilities were available due to rennovation

Reviewed on Jun 17, 2024

Holiday Inn Express Castro Valley - East Bay, an IHG Hotel

Holiday Inn Express Castro Valley - East Bay, an IHG Hotel

2.5 out of 5
per person
Aug 31 - Sep 5
found 2 hours ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
9.2/10 Wonderful! (518 reviews)
Very clean with a friendly staff

Reviewed on May 24, 2024

Hampton Inn Union City

Hampton Inn Union City

2.5 out of 5
per person
Aug 31 - Sep 5
found 2 hours ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
9.2/10 Wonderful! (1,000 reviews)
There was a car in the back of the hotel a Ford mustang it was there the four nights that we were there and and a man sleeping in the car, I didn’t feel safe, because I parked my car by the side. Everything else is was Excellent.thank you!!

Reviewed on Jun 15, 2024

Hampton Inn Oakland-Hayward

Hampton Inn Oakland-Hayward

2.5 out of 5
per person
Aug 31 - Sep 5
found 2 hours ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
9/10 Wonderful! (1,005 reviews)
The breakfast had a good selection of cold cereal , oatmeal, waffles and fruit but the hot items like the scrambled eggs and the sausage were not very good at all (could not eat them) the eggs tasted as if they were an artificial type non egg and sausage was not at all tasty, we ended up going out for breakfast the next day

Reviewed on Jun 18, 2024

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sonoma County Airport (STS)
Population
27,500
Max Temp Winter
60ºF
Max Temp Summer
80ºF
Top Sights
Safari West, Francis Ford Coppola Winery and Russian River Vineyard

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
Fully refundable
The price is $160 per night from Jul 7 to Jul 8
$160
$179 total
includes taxes & fees
Jul 7 - Jul 8
8.8/10 Excellent! (1,004 reviews)
"I stay here a lot when in Santa rosa n it's always comfortable n meets my needs for a very good price"

Reviewed on Jun 19, 2024

Holiday Inn Express® Windsor Sonoma Wine Country, an IHG Hotel
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
Fully refundable
The price is $151 per night from Jun 30 to Jul 1
$151
$169 total
includes taxes & fees
Jun 30 - Jul 1
8.8/10 Excellent! (579 reviews)
Great Stay
"Couldnt turn tv on, but wasn't a big deal. We didn't tell front desk until we checked out, so no problems on that end. No recycling bins in the room for recyclables. Bed was comfortable and room was clean. Quiet room even with hotel being so close to the freeway. Great stay all in all."

Reviewed on Jun 18, 2024

Holiday Inn Windsor Wine Country, an IHG Hotel
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 $161 per night from Jun 30 to Jul 1
$161
$180 total
includes taxes & fees
Jun 30 - Jul 1
9.2/10 Wonderful! (1,002 reviews)
"Convenient location to an event we were attending. Very comfortable room. Lobby was under construction, so breakfast location was modified. Still excellent!"

Reviewed on Jun 21, 2024

Hampton Inn & Suites Windsor - Sonoma Wine Country
See all 2,046 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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
Get set to book, because a trip to Windsor starts from a tempting $392. When you bundle your hotels, flights and car rentals into a package, you’ll enjoy the best prices.
How do I get a cheap travel package to Windsor?
Crafting your own Windsor vacation package with Expedia is one of the easiest ways to save. We have over 550 air carriers and 1,000,000 hotel options around the globe. With such a fantastic range to pick from, you’ll have no difficulty pulling together your ideal vacation.
Where should I stay in Windsor?
With so much to discover in Windsor, we suggest you book a room in a hotel near its attractions. Windsor Golf Club, Sonoma-Cutrer Vineyards Cutrer Vineyard and Pacific Coast Air Museum are some fascinating ones to put on your must-see list.
What are the top hotels in Windsor?
If it’s your very first time in Windsor, lock in a room at Windsor Wine Country Anthony Escape or Home Near Golf Course, Close To Healdsburg. Both hotels offer friendly service and are top options with many savvy travelers.
How far in advance should I book my Windsor vacation?
While not all air carriers advertise ticket prices early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you can bag some incredible deals. If you’ve left everything to the last minute, there’s a chance you could get lucky. Sometimes the lowest prices emerge just weeks before departure.
What does an Expedia Windsor travel package include?
Hotels, rental cars and flights — we’ve got them covered. With Expedia, you can shape your Windsor package just how you like it. All you have to do is figure out just what you need. Once you’ve made your booking, you can add on fun things like activities and experiences. The more you bundle, the greater your savings!
What should I know before booking a Windsor travel package?
You can save big by bundling your hotels, airfares and rental cars. Once you’ve made your booking, add on fun stuff like activities or sightseeing tours. Your next unforgettable vacation is only a couple of clicks away.
Can I choose my airline with a Windsor Expedia vacation package?
Yes, you sure can. We have more than 550 airline partners all over the world, so choose the carrier that’s a good fit for your needs.
If I'm not able to travel, can I cancel my Windsor vacation package?
If your travel plans in Windsor have changed, it’s good to know that it is possible to amend or cancel your booking. If you made your booking within the last 24 hours, you may be able to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge fees. For more information, visit our Customer Service Portal.

Discover the most 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 wineries.

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

What to do in Windsor

Image for Healdsburg Wine and Food Pairing Guided Walking Tour

Healdsburg Wine and Food Pairing Guided Walking Tour

$132
Per adult
98% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
Image for Bicycle Guided Tour in Napa and Sonoma

Bicycle Guided Tour in Napa and Sonoma

$200
Per adult
Bicycle Guided Tour in Napa and Sonoma
See all activities in Windsor

Other vacations you might like

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