Windermere Vacations from $1,122
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The Latest Windermere Vacation Packages
- Algonquin Lakeside Resort
Aug 28 - Sep 1Algonquin Lakeside Resort + Flight
Algonquin Highlands4 nights2.5 star property6.6/10 - (889 reviews)"Just outside of Algonquin Provincial Park. Place a bit tired and could use TLC"Reviewed July 25, 2026Roundtrip • Sioux Falls (FSD) - Muskoka District (YQA)FSD - YQA • 2 stops YQA - FSD • 2 stops$1,182$1,122found 8 hours agoper traveler - The Dudley Inn
Aug 28 - Sep 1The Dudley Inn + Flight
Muskoka Lakes4 nights2.5 star property9.8/10 - Exceptional (83 reviews)"Wonderful one night stay at the Dudley to see a concert at the Kee. No complaints. Beds and lines were very comfortable. Room was clean and well maintained. My only suggestion would be to add a floor length mirror or 1-2 mirrors in the room as the only mirror available to get ready was in the bathroom. We made it work as a party of 2 but it would be very challenging if a 3-4 girls stayed in the room."Reviewed July 20, 2026Roundtrip • Sioux Falls (FSD) - Muskoka District (YQA)FSD - YQA • 2 stops YQA - FSD • 2 stops$1,701$1,524found 8 hours agoper traveler - Muskoka Waterfront Retreat
Aug 28 - Sep 1Muskoka Waterfront Retreat + Flight
Lake of Bays4 nights3.0 star property8.6/10 - Excellent (108 reviews)"A nice place to stay at however too many rules and restrictions. Hey Mr Supervisor people can take a day or two off work to rest at this cottage so be considered and stop making up rules such as no fire to vibe made and no one can go kayaking due to the heat !! It's ridiculous to think that you can control everything! We have stayed there twice and each time our vacation is ruined by either no fire or no kayaking which defeats the whole purpose of a vacation . We didn't want to go all the way..."Reviewed July 26, 2026Roundtrip • Sioux Falls (FSD) - Muskoka District (YQA)FSD - YQA • 2 stops YQA - FSD • 2 stops$1,459$1,347found 8 hours agoper traveler - Rocky Crest Golf Resort
Aug 28 - Sep 1Rocky Crest Golf Resort + Flight
Seguin4 nights4.0 star property8.4/10 - Very Good (426 reviews)Roundtrip • Sioux Falls (FSD) - Muskoka District (YQA)FSD - YQA • 2 stops YQA - FSD • 2 stops$1,602$1,485found 8 hours agoper traveler - Touchstone Resort
Aug 28 - Sep 1Touchstone Resort + Flight
Muskoka Lakes4 nights4.0 star property8.6/10 - Excellent (426 reviews)"Beau site et superbe vue! Les installations manquent un peu d’amour. Le staff est au minimum et cela se voit. Il pourrait y avoir plus de temps alloué à l’entretien du site et des condos. Cuisine et douche sans escalier chaude pour la durée du séjour. Aucune excuse ou autre proposition!"Reviewed July 25, 2026Roundtrip • Sioux Falls (FSD) - Muskoka District (YQA)FSD - YQA • 2 stops YQA - FSD • 2 stops$1,886$1,753found 8 hours agoper traveler
Windermere Hotel Deals
Frequently Asked Questions
How much does a Windermere vacation package cost?
You can grab a vacation package to this destination from $1,122 on Expedia. But how much your vacation to Windermere costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Windermere?
If you'd like to score a cheap Windermere vacation package, consider visiting in September, November and December. You'll generally find lower prices on accommodations and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Windermere?
Usually, a handful of days is enough to check out the main sights during your Windermere vacation. But if you'd like to have time to chill out or go on day trips, think about extending your trip.
Is it worth booking a vacation package to Windermere?
Well known for its watersports, golfing and a host of other highlights, you can be certain Windermere is a good vacation destination. Some of the most popular attractions to put on your to-do list? Check out Windermere Golf & Country Club and Windermere Marina during your Windermere vacation.
How to find the best Windermere package deals?
Finding a cheap Windermere package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Windermere package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Windermere vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Windermere vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Windermere?
If you're considering a spontaneous Windermere adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Windermere vacation packages?
If you're like us, you love going away 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 the help of online lender Affirm, you can spread the cost of your Windermere vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you see them.