Windermere Vacations from $541
Book a Hotel + Flight or Car together to unlock savings
The Latest Windermere Vacation Packages
- Jolly Roger Inn & Resort
Aug 27 - Aug 31Jolly Roger Inn & Resort + Flight
Seguin4 nights3.5 star property8.0/10 - Very Good (708 reviews)"The continental breakfast was useless. People were shocked when they saw what was there for the breakfast. All they had was boiled eggs, cereal, waffles, bread , bagels, banana, apple and yoghurt. No sausages, cold cuts, potatoes and bacon. This place is useless. Won’t recommend to anyone for the price they charge!!!!!!!"Reviewed July 19, 2026Roundtrip • Austin (AUS) - Muskoka District (YQA)AUS - YQA • 1 stop YQA - AUS • 1 stop$602$541found 1 day agoper traveler - The Dudley Inn
Aug 27 - Aug 31The 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 • Austin (AUS) - Muskoka District (YQA)AUS - YQA • 1 stop YQA - AUS • 1 stop$1,172$990found 1 day agoper traveler - Rocky Crest Golf Resort
Aug 27 - Aug 31Rocky Crest Golf Resort + Flight
Seguin4 nights4.0 star property8.2/10 - Very Good (420 reviews)Roundtrip • Austin (AUS) - Muskoka District (YQA)AUS - YQA • 1 stop YQA - AUS • 1 stop$1,072$911found 1 day agoper traveler - Muskoka Waterfront Retreat
Aug 27 - Aug 31Muskoka Waterfront Retreat + Flight
Lake of Bays4 nights3.0 star property8.6/10 - Excellent (103 reviews)"We had an amazing stay! The staff is lovely and very efficient. The place was very clean. Beds were comfy and very clean as well. We had everything we needed and the beach was beautiful. There was always a canoe there when we wanted to go for a paddle no matter what time of day. (They were never all out) We had a fire every night. The lake is spectacular with the Oxtongue river just a 15 min paddle away. We hope to return in the near future."Reviewed July 19, 2026Roundtrip • Austin (AUS) - Muskoka District (YQA)AUS - YQA • 1 stop YQA - AUS • 1 stop$1,114$957found 1 day agoper traveler - Touchstone Resort
Aug 27 - Aug 31Touchstone Resort + Flight
Muskoka Lakes4 nights4.0 star property8.6/10 - Excellent (424 reviews)"Room was clean, but did have a bit of a smell at first, but it did seem to calm down after we had balcony door open for a bit. Staff did not advise that we could ask for towels to use at the pool. The rooms are positioned very high on the property, but unfortunately you can’t really see the lake due to the trees blocking the view. Kitchen in our unit was awesome. Room was very spacious. Really liked the layout of the living area and separate bedroom. The staff at the Touchstone Grill..."Reviewed July 16, 2026Roundtrip • Austin (AUS) - Muskoka District (YQA)AUS - YQA • 1 stop YQA - AUS • 1 stop$1,395$1,253found 1 day agoper traveler
Windermere Hotel Deals
JW Marriott The Rosseau Muskoka Resort & Spa
JW Marriott The Rosseau Muskoka Resort & Spa
Residence Inn by Marriott Gravenhurst Muskoka Wharf
Residence Inn by Marriott Gravenhurst Muskoka WharfFrequently Asked Questions
How much does a Windermere vacation package cost?
You can grab a vacation package to this destination from $541 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.