Winona Vacations from $306

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Winona vacation packages

Price found within the past 48 hours. Click for updated prices.
The Centennial

The Centennial

4 out of 5
Price was $439, price is now $306 per person
$306
per person
Jan 15 - Jan 18
found 15 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Manchester (MHT)
8.8/10 Excellent! (1,005 reviews)
Great stay at a wonderful Inn. The staff was lovely!

Reviewed on Nov 5, 2025

Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
Save 100% on your flight
Price was $528, price is now $362 per person
$362
per person
Jan 15 - Jan 18
found 15 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Manchester (MHT)
8.6/10 Excellent! (14 reviews)
Easy check-in, checkout; clean room; ready coffee machine! Quiet and cozy!

Reviewed on Nov 9, 2025

The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Save 100% on your flight
Price was $1,002, price is now $721 per person
$721
per person
Jan 15 - Jan 18
found 15 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Manchester (MHT)
9.6/10 Exceptional! (348 reviews)
Clean room. Luxurious and beautiful 😍

Reviewed on Oct 5, 2025

Perry's Motel and Cottages

Perry's Motel and Cottages

2.5 out of 5
Price was $1,070, price is now $806 per person
$806
per person
Jan 5 - Jan 9
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Manchester (MHT)
8.4/10 Very Good! (365 reviews)
Everything was perfect

Reviewed on Oct 21, 2025

Moultonborough Inn

Moultonborough Inn

3 out of 5
Price was $956, price is now $737 per person
$737
per person
Jan 5 - Jan 9
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Manchester (MHT)
9/10 Wonderful! (181 reviews)
Was an enjoyable stay. Staff was super helpful and informative. Really appreciated the supplies in the room like the coffee and utensils for use during the stay.

Reviewed on Oct 24, 2025

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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

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
$93 nightly
The price is $101 total per night from Nov 20 to Nov 21
$101 total
Nov 20 - Nov 21
Total with taxes and fees
8.8/10 Excellent! (939 reviews)
Yes

Reviewed on Nov 8, 2025

Best Western Plymouth Inn-White Mountains
Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

3 out of 5
281 Daniel Webster Hwy, Meredith, NH
$186 nightly
The price is $201 total per night from Dec 14 to Dec 15
$201 total
Dec 14 - Dec 15
Total with taxes and fees
8.2/10 Very Good! (901 reviews)
Room and staff were top notch, property was amazing. Will definitely return.

Reviewed on Nov 3, 2025

Mill Falls Resort Collection at the Lake
Winnisquam Lake Inn

Winnisquam Lake Inn

3 out of 5
788 Laconia Rd, Tilton, NH
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $92 total per night from Nov 16 to Nov 17
$92 total
Nov 16 - Nov 17
Total with taxes and fees
6.6/10 (799 reviews)
The room was clean. The property was centrally located and very affordable. I stayed during the off-season and the entire place to myself. The hotel offers beautiful views of Winnisquam Lake. It was great to watch the sunrise over the mountains in the morning.

Reviewed on Nov 6, 2025

Winnisquam Lake Inn
See all 1,837 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 from $306 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.