Winterland Vacations from $152

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The Latest Winterland vacation packages

Price found within the past 48 hours. Click for updated prices.
Horseshoe Las Vegas

Horseshoe Las Vegas

4 out of 5
Las Vegas Strip
Price was $584, price is now $152 per person
$152
per person
Nov 10 - Nov 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
7.8/10 Good! (10,691 reviews)
I’ve been visiting Vegas multiple times a month over the past couple decades. I’ve stayed at many hotels. The Horseshoe’s staff has hands down the most helpful and courteous staff I’ve ever had the pleasure to meet.

Reviewed on Sep 10, 2025

Paris Las Vegas Resort & Casino

Paris Las Vegas Resort & Casino

4 out of 5
Las Vegas Strip
Price was $517, price is now $186 per person
$186
per person
Nov 10 - Nov 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
8/10 Very Good! (23,552 reviews)
The checking is too tedious

Reviewed on Sep 10, 2025

The LINQ Hotel & Casino – A Caesars Rewards Destination

The LINQ Hotel & Casino – A Caesars Rewards Destination

4 out of 5
Las Vegas Strip
Price was $904, price is now $335 per person
$335
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
7.6/10 Good! (16,567 reviews)
The spa was amazing.

Reviewed on Sep 10, 2025

Harrah’s Las Vegas – A Caesars Rewards Destination

Harrah’s Las Vegas – A Caesars Rewards Destination

3.5 out of 5
Las Vegas Strip
Save 100% on your flight
Price was $343, price is now $153 per person
$153
per person
Nov 10 - Nov 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
7.8/10 Good! (13,136 reviews)
Nice casino hotel on LV Strip. A bit old vibe and atmosphere. Walkable to many restaurants and other attractions. Lobby hotel is hidden and hard to reach from the street.

Reviewed on Sep 10, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $11,784, price is now $5,359 per person
$5,359
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Miami (MIA)
8/10 Very Good! (1 review)
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Winterland Hotel Deals

Fantastic ocean view! Relax at this peaceful getaway

Fantastic ocean view! Relax at this peaceful getaway

Grand Beach
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Fantastic ocean view! Relax at this peaceful getaway
Home On The Pond

Home On The Pond

Grand Bank
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Home On The Pond
Take it easy at this tranquil getaway, only steps from the beach!

Take it easy at this tranquil getaway, only steps from the beach!

Grand Beach
Get rates
Take it easy at this tranquil getaway, only steps from the beach!
See all 7 properties in Winterland
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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Frequently asked questions

How much does a Winterland vacation package cost?
You can pick up a vacation package to this destination from $152 on Expedia. But how much your vacation to Winterland costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Winterland?
November, December and January are the best times to look for cheap Winterland vacation packages. Opting to travel in less busy periods means you can typically find lower prices on hotels and flights.
How many days is enough for Winterland?
With a well-planned itinerary, you can easily hit the main Winterland sights in a few days. But if you prefer to discover lesser-known spots or go on day trips, think about booking your Winterland vacation for longer.
How to find the best Winterland package deals?
Begin your search for a Winterland package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Winterland package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winterland escape off to a flying start.
Is it cheaper to book a Winterland vacation as a package?
You can enjoy significant savings on your Winterland retreat by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winterland?
If you have your Winterland travel dates confirmed, book early to score some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for impromptu escapes.
Does Expedia offer Book Now, Pay Later Winterland vacation packages?
Your Winterland break should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.