Winn Vacations

Book a Hotel + Flight or Car together to unlock savings

Winn Hotel Deals

Gateway Inn

Gateway Inn

2.5 out of 5
1963 Medway Road Medway ME
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $109 total per night from Dec 15 to Dec 16
$109 total
Dec 15 - Dec 16
Total with taxes and fees
8.4/10 Very Good! (432 reviews)
welcoming & friendly staff

Reviewed on Dec 7, 2025

Gateway Inn
Briarwood Motor Inn

Briarwood Motor Inn

2.5 out of 5
223 West Broadway Lincoln ME
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $120 total per night from Jan 2 to Jan 3
$120 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
8.8/10 Excellent! (181 reviews)
Room was clean and comfortable.

Reviewed on Dec 12, 2025

Briarwood Motor Inn
The Whitetail and Suites

The Whitetail and Suites

2.5 out of 5
67 West Broadway Lincoln ME
$119 nightly
The price is $129 total per night from Dec 15 to Dec 16
$129 total
Dec 15 - Dec 16
Total with taxes and fees
8.4/10 Very Good! (180 reviews)
towels made of sandpaper

Reviewed on Dec 3, 2025

The Whitetail and Suites
See all 75 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.

Find the Best Winn Vacation Packages

Winn Essential Information

Language
English
Currency
U.S dollars
Top Sights
Mt. Jefferson, Jato Highlands Golf Course and Lincoln Memorial Library

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Frequently asked questions

How much does a Winn vacation package cost?
You can pick up a vacation package to this destination on Expedia. But how much your vacation 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?
November, December and January are great times to search for cheap Winn vacation packages. Traveling in less busy months means you'll typically find reduced prices on flights and accommodations.
How many days is enough for Winn?
Usually, a handful of days is enough to tick off the main attractions during your Winn vacation. However, if you prefer to have some time to chill out or take day trips, think about extending your trip.
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 vacation package well in advance.
Is it cheaper to book a Winn vacation as a package?
You can enjoy significant savings on your Winn escape by booking a tailored vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Winn vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Winn break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.