A vineyard with rows of grapevines leading to a large, historic building surrounded by green hills.

Wine Country Luxury Vacations

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Top Luxury vacation packages in Wine Country

Price found within the past 48 hours. Click for updated prices.
  • Dec 24 - Dec 28

    The Estate Yountville + Flight

    Yountville
    4 nights
    5.0 star property
    9.4/10 - Exceptional (1,014 reviews)
    Roundtrip • Toronto (YYZ) - Oakland (OAK)
    YYZ - SFO • 1 stop SFO - YYZ • 1 stop
    CA $2,581
    CA $2,267
    per traveller
    found 17 hours ago
    The Estate Yountville
  • Dec 24 - Dec 28

    Solage, Auberge Collection + Flight

    Calistoga
    4 nights
    5.0 star property
    9.6/10 - Exceptional (773 reviews)
    Roundtrip • Toronto (YYZ) - Oakland (OAK)
    YYZ - SFO • 1 stop SFO - YYZ • 1 stop
    CA $3,140
    CA $2,715
    per traveller
    found 17 hours ago
    Solage, Auberge Collection
  • Dec 23 - Dec 28

    MacArthur Place Hotel & Spa + Flight

    Sonoma
    5 nights
    5.0 star property
    9.4/10 - Exceptional (890 reviews)
    Roundtrip • Toronto (YYZ) - Oakland (OAK)
    YYZ - OAK • 2 stops OAK - YYZ • 2 stops
    CA $4,646
    CA $4,033
    per traveller
    found 1 day ago
    MacArthur Place Hotel & Spa
  • Dec 24 - Dec 28

    Alila Napa Valley, a Hyatt Luxury Resort + Flight

    Downtown St. Helena
    4 nights
    5.0 star property
    9.2/10 - Wonderful (118 reviews)
    "Amaizing"
    Reviewed October 17, 2026
    Roundtrip • Toronto (YYZ) - Oakland (OAK)
    YYZ - SFO • 1 stop SFO - YYZ • 1 stop
    CA $3,935
    CA $3,426
    per traveller
    found 17 hours ago
    Alila Napa Valley, a Hyatt Luxury Resort
  • Dec 26 - Dec 30

    Okaeri Calistoga + Flight

    Calistoga
    4 nights
    5.0 star property
    10/10 - Exceptional (38 reviews)
    "A gem in Calistoga. Clean, well maintained property with a Japanese flair- mentally relaxing environment. Breakfast by Josh is OUTSTANDING. Craig, the property manager, is the nicest man, in addition to being totally service oriented. Despite the property being on the main road it is VERY quiet. The windows and walls are very well insulated. Bathroom with Japanese soaking tub was a treat!!! HIGHLY RECOMMENDED"
    Reviewed October 30, 2026
    Roundtrip • Toronto (YYZ) - Oakland (OAK)
    YYZ - SFO • 1 stop SFO - YYZ • 1 stop
    CA $3,161
    CA $2,779
    per traveller
    found 17 hours ago
    Okaeri Calistoga

Discover the most popular places to visit in Wine Country

What to do in Wine Country

Top Luxury Wine Country Hotels

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.

Plan the perfect luxury Wine Country vacation with Expedia

What are some benefits when booking luxury Wine Country vacations?

When you book a luxury Wine Country vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Wine Country?

If you're looking for something luxurious in Wine Country, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $2,267, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 12. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Wine Country. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Wine Country?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Wine Country.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Wine Country. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Wine Country?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Wine Country or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Wine Country. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.