Winona Vacation Packages

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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.

Top Winona Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Manchester-Bedford

Hampton Inn & Suites Manchester-Bedford

2.5 out of 5
Price was CA $1,175, price is now CA $1,080 per person
CA $1,080
per person
Oct 3 - Oct 6
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.4/10 Very Good! (1,003 reviews)
The beds were comfortable Carpeting in the halls were dirty

Reviewed on Aug. 17, 2025

The Centennial

The Centennial

4 out of 5
Price was CA $1,744, price is now CA $1,260 per person
CA $1,260
per person
Oct 3 - Oct 6
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
8.8/10 Excellent! (977 reviews)
Not a large chain Old nursing home

Reviewed on Aug. 20, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was CA $1,934, price is now CA $1,642 per person
CA $1,642
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Lebanon (LEB)
9/10 Wonderful! (727 reviews)
Remote location. Facilities were a good value.

Reviewed on Aug. 16, 2025

The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was CA $2,167, price is now CA $1,845 per person
CA $1,845
per person
Oct 3 - Oct 6
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
9.6/10 Exceptional! (342 reviews)
It was in a beautiful area.

Reviewed on May 30, 2025

Four Points by Sheraton Bedford Manchester Airport

Four Points by Sheraton Bedford Manchester Airport

3 out of 5
Price was CA $1,301, price is now CA $1,179 per person
CA $1,179
per person
Oct 3 - Oct 6
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
9/10 Wonderful! (61 reviews)
Great room for the price, microwave and refrigerator and Netflix plus other streaming options. Very nice accommodations!!!

Reviewed on Aug. 14, 2025

Ready to book your vacation to Winona?

 

Choose your dates

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
The price is CA $111 per night from Sep 7 to Sep 8
CA $111
CA $121 total
Sep 7 - Sep 8
includes taxes & fees
6.6/10 (694 reviews)
Winnisquam Inn
"The property is dated but clean. Staff was very friendly and helpful."

Reviewed on Aug. 12, 2025

Winnisquam Lake Inn
Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

3 out of 5
281 Daniel Webster Hwy, Meredith, NH
The price is CA $167 per night from Sep 4 to Sep 5
CA $167
CA $241 total
Sep 4 - Sep 5
includes taxes & fees
8.2/10 Very Good! (787 reviews)
"Attended a concert at BNP...was very convenient for late night bed-down and exploring the region the next day. Church Landing checkin not a problem until the keys fail, then it's a hassle to be at Palmer Inn, but Erica was very responsive and pleasant for replacement."

Reviewed on Aug. 19, 2025

Mill Falls Resort Collection at the Lake
Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

2.5 out of 5
480 Main Street, Laconia, NH
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Sep 7 to Sep 8
CA $158
CA $171 total
Sep 7 - Sep 8
includes taxes & fees
7.6/10 Good! (1,007 reviews)
"Staff friendly. Beds extremely comfortable. Very clean. Pool nice size. Only negative is breakfast served too late for me to take advantage. Centrally located"

Reviewed on Aug. 14, 2025

Best Western Plus Landmark Inn
See all 1,885 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.
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Frequently asked questions

How much does a Winona vacation package cost?
You'll find cheap prices from CA $1,080 on Expedia for your Winona break. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Winona costs.
What are the cheapest months to go to Winona?
If you're looking to snag a cheap Winona vacation package, consider travelling in January, February and March. You'll typically find better prices on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Winona?
With a well-organized schedule, you can easily visit the most popular Winona attractions in a handful of days. But if you'd like to discover hidden gems or go on day tours, think about booking your Winona vacation for longer.
How to find the best Winona package deals?
Bagging a cheap Winona package deal is easy with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most affordable Winona package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Winona vacation as a package?
You can enjoy significant savings on your Winona break by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to browse some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Winona?
If you've got your Winona vacation dates locked in, book early to snap up some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Winona?

  1. Choose your travel dates: The things you'd like to do in Winona and your favourite season will help you decide when to get away.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and food to flights and activities. Your accommodations will probably be the biggest expense during your trip to Winona.
  3. Decide how long to go away for: Now that you're up to speed on Winona, you can figure out the ideal length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to see.
  4. Combine your accommodations and airfare: Once you've nailed down your travel dates and duration, book the ideal Winona vacation package for you.

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