Windermere Vacations from $439

Book a Hotel + Flight or Car together to unlock savings

The Latest Windermere Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 18 - Sep 22

    Tay Motel + Flight

    Severn
    4 nights
    2.5 star property
    8.6/10 - Excellent (56 reviews)
    Roundtrip New York (NYC) - Muskoka District (YQA)
    LGA - YQA1 stop YQA - LGA1 stop
    $516
    $439
    per traveler
    found 1 day ago
    Tay Motel
  • Sep 18 - Sep 22

    Windermere House + Flight

    Muskoka Lakes
    4 nights
    3.5 star property
    9.2/10 - Wonderful (1,001 reviews)
    "Always a beautiful stay at windemere!"
    Reviewed July 30, 2026
    Roundtrip New York (NYC) - Muskoka District (YQA)
    LGA - YQA1 stop YQA - LGA1 stop
    $1,250
    $1,108
    per traveler
    found 13 hours ago
    Windermere House
  • Sep 18 - Sep 22

    Muskoka Waterfront Retreat + Flight

    Lake of Bays
    4 nights
    3.0 star property
    8.4/10 - Very Good (110 reviews)
    Roundtrip New York (NYC) - Muskoka District (YQA)
    LGA - YQA1 stop YQA - LGA1 stop
    $798
    $732
    per traveler
    found 13 hours ago
    Muskoka Waterfront Retreat
  • Sep 18 - Sep 22

    Algonquin Lakeside Resort + Flight

    Algonquin Highlands
    4 nights
    2.5 star property
    6.6/10 - (895 reviews)
    Roundtrip New York (NYC) - Muskoka District (YQA)
    LGA - YQA1 stop YQA - LGA1 stop
    $645
    $598
    per traveler
    found 13 hours ago
    Algonquin Lakeside Resort
  • Sep 18 - Sep 22

    Happyland Inn + Flight

    Severn
    4 nights
    2.0 star property
    7.4/10 - Good (106 reviews)
    Roundtrip New York (NYC) - Muskoka District (YQA)
    LGA - YQA1 stop YQA - LGA1 stop
    $548
    $514
    per traveler
    found 13 hours ago
    Happyland Inn

Windermere Hotel Deals

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.

Frequently Asked Questions

How much does a Windermere vacation package cost?

You can grab a vacation package to this destination from $439 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.

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