Winona Vacations

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Your Winona Vacation

From its highlights to its hidden gems, this city is best explored with a Winona vacation package. Check out places to stay in Tenney Mountain, which is good for nature, views and hiking. When it's time to head out and see the sights, be sure to put Scribner-Fellows State Forest and Waukewan Golf Club on the to-do list for your trip to Winona. Whoever you're escaping with and whether your budget is big or small, your dream Winona vacation is just a few clicks away with Expedia.

Discover the most popular places to visit in Winona

Scribner-Fellows State Forest

Explore the great outdoors at Scribner-Fellows State Forest and enjoy the mountain views during your trip to New Hampton. While you're in the area, stroll along the lakeside.

Scribner-Fellows State Forest

Winona Hotel Deals

Winnisquam Lake Inn

Winnisquam Lake Inn

3 out of 5
788 Laconia Rd Tilton NH
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $97 total per night from Jan 1 to Jan 2
$97 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
6.6/10 (816 reviews)
Excellent

Reviewed on Dec 4, 2025

Winnisquam Lake Inn
Best Western Plymouth Inn-White Mountains

Best Western Plymouth Inn-White Mountains

2.5 out of 5
1513 US Route 3 Campton NH
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $108 total per night from Jan 4 to Jan 5
$108 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.8/10 Excellent! (967 reviews)
Very nice place!

Reviewed on Dec 22, 2025

Best Western Plymouth Inn-White Mountains
The Common Man Inn & Spa

The Common Man Inn & Spa

4 out of 5
231 Main St Plymouth NH
$121 nightly
The price is $131 total per night from Jan 12 to Jan 13
$131 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
9/10 Wonderful! (388 reviews)
This was a beautiful cozy place to be. The continental breakfast was excellent and the place was beautiful.

Reviewed on Dec 20, 2025

The Common Man Inn & Spa
See all 1,818 properties in Winona
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 Winona Vacation Packages

Winona Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Winona vacation package cost?
You'll find cheap prices on Expedia for your Winona break. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Winona costs.
What are the cheapest months to go to Winona?
October, November and December are great times to search for cheap Winona vacation packages. Choosing to travel in quieter periods means you can generally find reduced prices on hotels and flights.
How many days is enough for Winona?
The ideal length of your Winona vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you plenty of time to go to all the leading attractions and discover some hidden treasures along the way.
How to find the best Winona package deals?
Begin your search for a Winona package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Winona package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Winona getaway off to a flying start.
Is it cheaper to book a Winona vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Winona vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Winona?
Enjoy fantastic discounts by booking your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Winona break.
Does Expedia offer Book Now, Pay Later Winona vacation packages?
Jet off on your perfect escape to Winona with our Book Now, Pay Later vacations. No need to save up or hold off until payday — we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, you can easily budget for your trip and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.