Windsor Holidays from £976
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Your Windsor Holiday
Uncover the best parts of Windsor with a customised Windsor holiday 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 holiday to Windsor now.
Top Windsor Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Claremont Resort & Club
Claremont Hills
£976
per person
20 Nov - 25 Nov
found 24 hours ago
Return flight included
London (LON) to Oakland (OAK)
9/10 Wonderful! (1,101 reviews)
It’s always a joy to stay at the Claremont. Such an amazing location and building. It’s like going back in time to more elegant and sophisticated age. The service is always friendly, but restrained. The rooms are clean. The grounds are verdant and well kept,
Reviewed on 9 Sept 2026
Okaeri Calistoga
£1,661
per person
19 Oct - 23 Oct
found 21 hours ago
Return direct flight included
London (LON) to Oakland (OAK)
10/10 Exceptional! (29 reviews)
We had a wonderful stay! The room was very clean, comfortable, and well maintained. The staff were incredibly friendly, welcoming, and always helpful whenever we needed anything. Breakfast was delicious with a great selection and was a perfect way to start the day. Overall, we had a great experience and felt very well taken care of. I would absolutely stay here again and highly recommend it!
Reviewed on 6 Sept 2026
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Sonoma County Airport (STS) |
Population | 27,500 |
Max Temp Winter | 16ºC |
Max Temp Summer | 27ºC |
Top Sights | Safari West, Francis Ford Coppola Winery and Russian River Vineyard |
Top hotels in Windsor
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane Windsor CA
Fully refundable
£107
13 Sept - 14 Sept
includes taxes & fees
9.2/10 Wonderful! (1,322 reviews)
"Room was nice, clean and they were able to accommodate the first floor. Very comfortable pillows - (meant to ask where I could buy a couple!). Pool area was okay - hot spa was nice and warm. Breakfast was basic, not the best, but not the worst we've ever had."
Reviewed on 9 Sept 2026
Hampton Inn & Suites Windsor - Sonoma Wine Country
8937 Brooks Road South Windsor CA
Fully refundableReserve now, pay when you stay
£124
20 Sept - 21 Sept
includes taxes & fees
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy Windsor CA
Fully refundable
£117
14 Sept - 15 Sept
includes taxes & fees
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)
Russian Hill Estate crafted acclaimed Pinot Noir and Syrah from Sonoma's Russian River Valley terroir. Visitors enjoyed intimate tastings with vineyard views and picnic areas perfect for savouring their distinctive wines.
Windsor Golf Club
8.8/10 (19 reviews)
This championship course winds through Sonoma wine country, challenging golfers with scenic water hazards and majestic oaks. Enjoy innovative cuisine at Charlie's Restaurant overlooking the countryside.
La Crema Estate at Saralee's Vineyard
This historic barn-turned-tasting room showcases La Crema's acclaimed cool-climate wines in Russian River Valley. Savour vineyard views while experiencing guided tastings or speciality pairings.
Pacific Coast Air Museum
10.0/10 (4 reviews)
The Pacific Coast Air Museum displays meticulously preserved aircraft spanning decades of aviation history. Climb into cockpits during "Open Cockpit Day" events for a pilot's perspective.
Windsor Oaks Vineyards
9.6/10 (5 reviews)
This estate produces premium wines across three appellations, with various grapes thriving in diverse microclimates. Visit during exclusive open days to savour handcrafted wines amid preserved natural beauty.
Martinelli Vineyard
8.6/10 (4 reviews)
Housed in a historic hop barn, Martinelli Winery showcases five generations of family winemaking expertise. Sample their estate-grown Pinot Noir and Zinfandel while learning about 135 years of viticultural heritage.
Powell's Sweet Shoppe - Windsor
10.0/10 (7 reviews)
Powell's Sweet Shoppe transported visitors to a sweets wonderland with nostalgic treats and vintage toys. The shop's continuous playing of "Charlie and the Chocolate Factory" created a whimsical atmosphere for all ages.
Guerro Fernandez
You can enjoy a tasting or tour at Guerro Fernandez during your travels to Windsor. Visit the wineries or top-notch restaurants in this family-friendly area.
What to do in Windsor
Sonoma County Wine Tour: Self-Guided GPS Audio Driving Guide
£22
per traveller
Sonoma County, CA: Outdoor Stargazing and Astronomy Tour
£69
per adult
Frequently asked questions
How much does a Windsor travel package cost?
We make it simple for everyone to travel, with Windsor packages starting from just £976. You'll have the flexibility to combine your preferred airlines, hotels and car rental. For the ultimate escape, why not add a few activities and tours to your travel itinerary?
If I'm not able to travel, can I cancel my Windsor travel package?
It's difficult to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Windsor travel package. If you booked in the last 24 hours, you may be entitled to a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for more information.
How do I get a cheap travel package to Windsor?
You'll save tons of cash if you combine your hotels, car rentals and flights into a Windsor travel package. Sometimes cheap means fewer options. But not with Expedia. We offer more than 550 partner airlines and 1,000,000 hotels all over the world, so you'll always have plenty of options to choose from. Like to save even more? Add some exciting activities to your package deal to unlock even more discounts! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Windsor holidays?
Expedia has partnered with online lender Klarna to make your next trip easier on the purse strings. Paying in instalments means you can spread the costs of your next big holiday, leaving you with more money to spend while you're travelling. Klarna has several payment plans to pick from, so you're sure to find one that fits into your budget. Take a look at these flexible payment options:
- Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna offers just that! Paying in easy monthly instalments will make your holiday dreams come true.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your trip in multiple transactions.
- Low deposit holidays: When you come across an incredible deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock in your escape.
Where should I stay in Windsor?
With interesting attractions such as Windsor Golf Club and Sonoma-Cutrer Vineyards Cutrer Vineyard in this neighbourhood, look for a hotel positioned near either of them. Windsor Oaks Vineyards is another Windsor hot spot that pulls the crowds.
What are the top hotels in Windsor?
The Inn at the Tides and Good Nite Inn Rohnert Park are among the most well-known hotels in Windsor. Why not take a look at the rates and facilities at each and then make up your mind?
How far in advance should I book my Windsor holiday?
It can be hard to know exactly when the best time is to book your trip to Windsor. But generally the earlier you book, the more affordable the prices. Sometimes, you can lock in your flights and hotels up to 12 months prior to departure. If you're hoping for a last-minute getaway, no need to fret! There are great deals featured on Expedia all the time.
What does an Expedia Windsor travel package include?
Flights, hotels and rental cars — we've got them all. With Expedia, you can create your Windsor travel package the way you want. All you have to do is figure out what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the bigger your savings!
What should I know before booking a Windsor travel package?
Our prices are always low. However, you'll enjoy even more bargains when you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Windsor Expedia travel package?
Expedia has access to more than 550 airline partners globally, so you certainly can. Just select your favourite carrier and put together the perfect Windsor getaway.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
