Winn Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Winn Holiday

Our pick of the best Winn Hotel Deals

Gateway Inn
Gateway Inn
2.5 out of 5
1963 Medway Road, Medway, ME
Fully refundableReserve now, pay when you stay
The price is NZ$180 per night from 8 July to 9 July
NZ$180
8 July - 9 July
includes taxes & fees
8.2/10 Very Good! (377 reviews)
"Old, but in a good way."

Reviewed on 2 Jul. 2025

Gateway Inn
Lakefront home with something to enjoy for every season!
Lakefront home with something to enjoy for every season!
Lee
9.6/10 Exceptional! (160 reviews)
Beautiful peaceful home on lake
"This property was absolutely beautiful. The homes open concept with cathedral ceilings are gorgeous. The lake view from the bedroom upstairs is so relaxing. More than i imagined. We will definitely be back to enjoy this property and all the lake has to offer. The hosts are amazing as well."

Reviewed on 3 May 2025

Get rates
Lakefront home with something to enjoy for every season!
Schlafmans Hollow Solar Cabins
Schlafmans Hollow Solar Cabins
3 out of 5
387 Main St, Lincoln, ME
The price is NZ$150 per night from 21 July to 22 July
NZ$150
21 July - 22 July
includes taxes & fees
9.8/10 Exceptional! (12 reviews)
"schlafman's hollow stay was very pleasant scott the propriator was very nice an' communicative would stay again an' have already recommended to others"

Reviewed on 10 Jun. 2025

Schlafmans Hollow Solar Cabins
See all 73 properties in Winn
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 Winn holiday package cost?
You can pick up a holiday package to this destination on Expedia. But how much your holiday to Winn costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Winn?
You can generally find lower prices and better availability in January, February and March. Explore our cheap Winn holiday packages and you could score some great off-season deals.
How many days is enough for Winn?
With a well-planned itinerary, you can easily visit the top Winn sights in a handful of days. But if you'd like to venture off the beaten track or take day trips, consider booking your Winn holiday for longer.
How to find the best Winn package deals?
Use Expedia's handy filters to find some of the best Winn package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Winn package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Winn holiday as a package?
You can enjoy significant savings on your Winn escape by booking a tailored holiday package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Winn?
If you're planning an impromptu Winn adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Winn?

  1. Pick your dates: The things you plan to do in Winn and your favourite season will help you decide when to go.
  2. Budget wisely: On top of the price of your hotel, you should consider other expenses too. These include transportation, flights and food. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Winn.
  3. Decide how long to go for: Now that you're more familiar with Winn, you can figure out the perfect length of your holiday. Pull together a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your accommodation and airfare: After you've settled on your dates and duration, lock in the perfect Winn holiday package for you.

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