Windermere Vacations from $444
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The Latest Windermere Vacation Packages
- Tay Motel
Sep 18 - Sep 22Tay Motel + Flight
Severn4 nights2.5 star property8.6/10 - Excellent (55 reviews)"The positives: Clean bed, linens and overall general upkeep was good. The negatives: Some standard items that I would have expected were missing. There was no full length mirror in the room to double check your outfit before heading out. I also didn't an ironing board or iron but this might be available at the front desk, I didn't ask as I didn't need it. There was no coffee maker or kettle in the room. 2 bottles of water were provided and a mini fridge. The staff mentioned there was a Tims..."Reviewed July 1, 2026Roundtrip • New York (NYC) - Muskoka District (YQA)EWR - YQA • 1 stop YQA - LGA • 1 stop$522$444found 12 hours agoper traveler - The Dudley Inn
Sep 23 - Sep 28The Dudley Inn + Flight
Muskoka Lakes5 nights2.5 star property9.8/10 - Exceptional (81 reviews)"Great room. Had everything we needed. Lots of outdoor seating and places for fires. Highly recommend"Reviewed July 16, 2026Roundtrip • New York (NYC) - Muskoka District (YQA)LGA - YQA • 1 stop YQA - EWR • 1 stop$924$762found 9 hours agoper traveler - Sunnylea Resort
Sep 18 - Sep 22Sunnylea Resort + Flight
Georgian Bay4 nights2.5 star property8.4/10 - Very Good (92 reviews)"We loved the pool and the easy access to the water toys like kayaks and paddle boards. They supplied the life jackets which was helpful and supplied all the linens, towels and even provided soap and shampoo. It is a beautiful firepit and nice sandy volleyball pit. There isn’t swimming off the dock, as the water is full of reeds but the water is clean and lots of opportunities to go out into deeper water to swim. We loved it!"Reviewed July 7, 2026Roundtrip • New York (NYC) - Muskoka District (YQA)EWR - YQA • 1 stop YQA - LGA • 1 stop$802$680found 12 hours agoper traveler - Severn Lodge
Sep 18 - Sep 22Severn Lodge + Flight
Port Severn4 nights3.5 star property10/10 - Exceptional (1 review)"Came here for the first time my family. Amazing place. Lots of stuff to do. Very kids friendly. Definitely recommend;"Reviewed June 29, 2026Roundtrip • New York (NYC) - Muskoka District (YQA)EWR - YQA • 1 stop YQA - LGA • 1 stop$1,008$889found 12 hours agoper traveler - Rocky Crest Golf Resort
Aug 28 - Sep 1Rocky Crest Golf Resort + Flight
Seguin4 nights4.0 star property8.2/10 - Very Good (417 reviews)Roundtrip • Sioux Falls (FSD) - Muskoka District (YQA)FSD - YQA • 2 stops YQA - FSD • 2 stops$1,819$1,659found 17 hours agoper traveler
Windermere Hotel Deals
Howard Johnson by Wyndham Gravenhurst
Howard Johnson by Wyndham Gravenhurst
Frequently Asked Questions
How much does a Windermere vacation package cost?
You can grab a vacation package to this destination from $444 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.