Monterey Wine Country Luxury Vacations

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Flight and Luxury hotel deals in Monterey Wine Country

Price found within the past 48 hours. Click for updated prices.
Monterey Beach Hotel, A Tribute Portfolio Hotel

Monterey Beach Hotel, A Tribute Portfolio Hotel

CA $2,114
per person
Oct 21 - Oct 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Francisco (SFO)
8.6/10 Excellent! (790 reviews)
Hyatt Regency Monterey Hotel & Spa

Hyatt Regency Monterey Hotel & Spa

CA $2,197
per person
Oct 21 - Oct 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Francisco (SFO)
8.6/10 Excellent! (1,725 reviews)
The Quail

The Quail

CA $3,105
per person
Oct 21 - Oct 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Monterey (MRY)
9.6/10 Exceptional! (1,010 reviews)
Staff was very kind and helpful. It was very peaceful and quiet and very beautiful to sit and watch the sunset or even take a dinner walk. Rooms were clean and bed was comfortable. We had a shower water overflow problem at night and they made sure to get us to another room right away and help us with our bags while moving over rooms. Great place and i would 100% stay here again. Thank you to the great staff for making this such a pleasant stay!

Reviewed on Sep 11, 2026

Portola Hotel & Spa at Monterey Bay

Portola Hotel & Spa at Monterey Bay

Downtown Monterey
CA $2,381
per person
Oct 21 - Oct 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Francisco (SFO)
9.2/10 Wonderful! (3,634 reviews)
InterContinental the Clement Monterey by IHG

InterContinental the Clement Monterey by IHG

New Monterey
CA $2,403
per person
Oct 21 - Oct 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Francisco (SFO)
9.4/10 Exceptional! (1,182 reviews)
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3 Night Luxury holidays in Monterey Wine Country

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Monterey Hotel & Spa

Hyatt Regency Monterey Hotel & Spa

CA $1,199
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to San Francisco (SFO)
8.6/10 Excellent! (1,725 reviews)
Carmel Valley Ranch, in The Unbound Collection by Hyatt

Carmel Valley Ranch, in The Unbound Collection by Hyatt

CA $3,087
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Monterey (MRY)
9/10 Wonderful! (823 reviews)
The property grounds are beautiful and well maintained. Lots to do. Great hiking trails around. The main building "the lodge" where reception, restaurant and spa are is very nice, contemporary and well maintained. The issue is the rooms. We got a "vineyard oak studio with outside tub". The rooms are VERY dark and cavernous despite the sliding door window. The view is also mainly completely blocked by oak trees. Based on the layout of the property I don't think there is actual vineyard views, most are oak trees, which is great except it makes the rooms very dark. Don't expect to get the views from the marketing pictures, maybe there's just a couple like that. The rooms themselves are VERY tired. Think 2000's stripe brown carpet (questionable). A random sofa floating in the room. A tiny little "art" frame that goes with nothing on a huge wall...Can't possibly have been decorated by an interieur decorator worth that name. Outside chairs/cushions are destroyed. For those prices, the room feel more like a $199/night hotel at best. A renovation is WAY overdue to command those prices. We saw a different room in another part of property, which was the same. The rest of the property is lovely though.

Reviewed on Sep 4, 2026

The Quail

The Quail

CA $1,347
per person
Oct 26 - Oct 29
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Monterey (MRY)
9.6/10 Exceptional! (1,010 reviews)
Staff was very kind and helpful. It was very peaceful and quiet and very beautiful to sit and watch the sunset or even take a dinner walk. Rooms were clean and bed was comfortable. We had a shower water overflow problem at night and they made sure to get us to another room right away and help us with our bags while moving over rooms. Great place and i would 100% stay here again. Thank you to the great staff for making this such a pleasant stay!

Reviewed on Sep 11, 2026

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4 Night Luxury holidays in Monterey Wine Country

Price found within the past 48 hours. Click for updated prices.
Hotel Pacific

Hotel Pacific

Downtown Monterey
CA $3,301
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to San Francisco (SFO)
8.2/10 Very good! (1,812 reviews)
We've been here twice. The first time, about a year ago the room was amazing! Great view of the ocean. I booked the same category room (King Jr. Suite) for this 1 day stay. Man, we got the armpit of the rooms. Monterey was hotter usual, and apparently this hotel doesn't have AC. We left the patio door open, but there is no screen, so--mosquitoes. No screen on the window either. And the patio looked at a wall and the parking lot? of another hotel? So I went to the office about the hot box we were in, and we got a box fan. Which was okayyy. Then we noticed that the bed had one normal actual pillow and 3 other pillows that were "half pillows" on the king sized bed. Not standard pillows , half sized of 1 standard pillow size. The TV only showed programs (and commercials, I swear it) from 20 years ago, or Fox. If you like Fox, you could watch whatever was on Fox all night. I could not cast anything to the TV from my phone. THEN the walls are pretty thin in this room...so we got to hear our neighbors taking showers, flushing toilets and puking their guts up this morning. I assume their could hear us, too. (except for getting sick). Overall, one of my more miserable hotel stays in quite a long while.

Reviewed on Sep 11, 2026

Hyatt Regency Monterey Hotel & Spa

Hyatt Regency Monterey Hotel & Spa

CA $3,394
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to San Francisco (SFO)
8.6/10 Excellent! (1,725 reviews)
The Quail

The Quail

CA $3,598
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Monterey (MRY)
9.6/10 Exceptional! (1,010 reviews)
Staff was very kind and helpful. It was very peaceful and quiet and very beautiful to sit and watch the sunset or even take a dinner walk. Rooms were clean and bed was comfortable. We had a shower water overflow problem at night and they made sure to get us to another room right away and help us with our bags while moving over rooms. Great place and i would 100% stay here again. Thank you to the great staff for making this such a pleasant stay!

Reviewed on Sep 11, 2026

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Plan the perfect luxury Monterey Wine Country vacation with Expedia

What are some benefits when booking luxury Monterey Wine Country vacations?

When you book a luxury Monterey 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 Monterey Wine Country?

If you're looking for something luxurious in Monterey 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 $1,199, 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 9. 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 Monterey 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 Monterey 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 Monterey Wine Country.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Monterey 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 Monterey 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 Monterey 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 Monterey 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.

Luxury Hotels in Monterey Wine Country

L Auberge Carmel

L Auberge Carmel

Monte Verde at Seventh Carmel CA
  • 11 min drive from Monterey Bay Aquarium
Book a stay at this luxury hotel in Carmel. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.2/10 Wonderful! (594 reviews)
"Unacceptable lack of privacy. The restaurant staff walkway is directly next to back window of the room, with workers talking and looking into room window. There is no AC in the room and I couldn't keep the windows or shades open due to lack of privacy. Restaurant recycling and grease container are ..."

Reviewed on Sep 9, 2026

L Auberge Carmel
Monterey Plaza Hotel & Spa

Monterey Plaza Hotel & Spa

400 Cannery Row Monterey CA
  • 9 min walk from Monterey Bay Aquarium
Book a stay at this luxury resort in Monterey. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (1,677 reviews)
"Elite class resort. From the valet parking, to the bell service, to the housekeeping staff. Everything was top notch here. The rooms are gorgeous….spend a little extra for an ocean view. Restaurants are amazing and there’s even a complimentary bike rental for guests. I will definitely be back"

Reviewed on Sep 12, 2026

Monterey Plaza Hotel & Spa
The Monterey Hotel

The Monterey Hotel

407 Calle Principal Monterey CA
  • 26 min walk from Monterey Bay Aquarium
Stay at this hotel in Monterey. Enjoy free WiFi, a fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in ...
8/10 Very good! (1,791 reviews)
"Beware! This hotel has NO a/c, and an elevator on one side only. Rooms have ceiling fans, and windows with no screens. Gnats in bathroom, and coffee area. Upon check-in,the two men were super nice and helpful. The next morning, a man and women, didn’t even greet us when we walked past. The coffee ..."

Reviewed on Sep 10, 2026

The Monterey Hotel
See all 1,170 properties in Monterey Wine Country
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.

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