Windsor Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Windsor

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 S$190 per night from 1 Dec to 2 Dec
S$190
includes taxes & fees
1 Dec - 2 Dec
8.8/10 Excellent! (1,007 reviews)
"Close to main stores, freeway and good restaurants"

Reviewed on 21 Nov,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 S$177 per night from 1 Dec to 2 Dec
S$177
includes taxes & fees
1 Dec - 2 Dec
8.8/10 Excellent! (752 reviews)
"Great stay"

Reviewed on 22 Nov,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 S$195 per night from 8 Dec to 9 Dec
S$195
includes taxes & fees
8 Dec - 9 Dec
9.2/10 Wonderful! (1,003 reviews)
"Property was very nice. Brian at the front desk was excellent. I stayed in an accessible studio beautiful spacious. Only thing I saw that needed to be fixed was inside the bathroom on the walls. Either mold mildew something towards the ceiling."

Reviewed on 20 Nov,2024

Hampton Inn & Suites Windsor - Sonoma Wine Country
See all 2,079 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.

Frequently asked questions

How much does a Windsor holiday package cost?
Get set to book, because a trip to Windsor starts from a tempting . 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 holiday 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 holiday.
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 travellers.
How far in advance should I book my Windsor holiday?
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 holiday is only a couple of clicks away.
Can I choose my airline with a Windsor Expedia holiday 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 holiday 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.

What to do in Windsor

Fine wines paired with tapas-sized portions of food

Icon Wine & Food Pairing at Williamson Wines in Healdsburg

S$67
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

S$314
Per adult
100% of travellers recommend
Giant Redwoods Tour Including a 5-Course Winery Lunch
Healdsburg Wine and Food Pairing Walking Tour

Healdsburg Wine and Food Pairing Guided Walking Tour

S$177
Per adult
96% of travellers recommend
Healdsburg Wine and Food Pairing Guided Walking Tour
See all activities in Windsor

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.