Windermere Vacations from $1,051
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Your Windermere Vacation
Enjoy unforgettable adventures when you book a Windermere vacation package. Whether you're a foodie, art enthusiast or just a traveler who loves experiencing new places, there's something for everyone in this interesting city. If a sightseeing tour is on the to-do list during your trip to Windermere, swing by big attractions like Lake Joseph Golf Club, Diamond In The Ruff Golf Course and The Port Carling Wall. Expedia is here to help you escape the everyday. Tailor your vacation to Windermere to suit your travel style, whatever that may be.
The Latest Windermere vacation packages
Price found within the past 48 hours. Click for updated prices.
Haliburton Post House
$1,329
per person
Oct 6 - Oct 13
found 1 hour ago
Roundtrip flight included
Jacksonville (JAX) to Muskoka (YQA)
10/10 Exceptional! (3 reviews)
Recently stayed here Aug. 14-16. Check in was seamless. A pair of chocolate truffles welcomed us on arrival with a hand written note saying as much. The mattress was firm and in excellent condition, the room was fully pre-stocked stocked with crisp, fresh linens and a mini fridge with several non-alcoholic drinks at no extra charge, coffee pods and a coffee maker. The room and washroom sparkled and smelled of fresh cedar logs, instantly transporting us into Vacay Mode. The complimentary brekky was fresh and generous enough to let us get going on our early morning paddle to explore the lake by canoe or kayak. Fresh, plush towels were available outdoors, too, right near the dock. The sauna located in the gym, the outdoor fireplace and games would also be great to try during a longer stay. I can suggest to offer guests to make marshmallows in summer by the firepit one night of the week. Front of House lead, Justine, took very good care of us and responded to any request we made and checked back in during our stay, in case we wanted to opt in for dinner or brunch reservations. Very attentive staff overall. Would go back here in a heartbeat in another season to continue exploring the area. A magical hidden gem in Haliburton that actually does live up to its 5 star rating. Outstanding service by the whole team. I cannot wait to tell my close friends how wonderful our visit here was.
Reviewed on Aug 18, 2026
Rocky Crest Golf Resort
$1,150
per person
Oct 6 - Oct 13
found 7 hours ago
Roundtrip flight included
Jacksonville (JAX) to Muskoka (YQA)
8.4/10 Very Good! (431 reviews)
The room is clean and well maintained. The staff is very friendly and helpful with questions. The foods are delicious and deserve the prices. The lake view is fantastic. My son loves the water castle and we will definitely come back next year!
Reviewed on Aug 17, 2026
White Birches Cottages
$1,455
per person
Oct 6 - Oct 13
found 1 hour ago
Roundtrip flight included
Jacksonville (JAX) to Muskoka (YQA)
8.2/10 Very Good! (13 reviews)
Stayed with my family for two nights. The cottage is very quiet even though the cottages are located in close proximity to each other. The check in and check out was simple and easy. There are plenty of water activities available to take part in (paddle board, canoes, and kayak). We would stay here again.
Reviewed on Oct 11, 2025
Stay near popular Windermere attractions
Windermere Golf & Country Club
8.8/10 (29 reviews)
Enjoy a round of golf in Windermere at Windermere Golf & Country Club. Stroll along the lakeside or visit the spas in this family-friendly area.
Windermere Marina
8.4/10 (48 reviews)
Explore the waterfront in Windermere with a trip to Windermere Marina. Stroll along the lakeside in this relaxing area, or seek out the golf courses.
What to do in Windermere
Private 4 Day Algonquin Park Backcountry Canoe Trip
$1,062
per adult
Windermere Hotel Deals
Windermere House
2508 Windermere Road Muskoka Lakes ON
Fully refundableReserve now, pay when you stay
$278 nightly
$314 total
Sep 7 - Sep 8
Total with taxes and fees
Muskoka Tiny Home
Windermere ON
9.6/10 Exceptional! (8 reviews)
"Very clean and modern Nice location."
Reviewed on Aug 7, 2026
Charming Muskoka Wilderness Cottage
Windermere ON
9.6/10 Exceptional! (12 reviews)
"We really enjoyed our little getaway and found the cottage to be a lovely, peaceful place to relax. It was clean, updated, comfortable, and welcoming when we arrived. The property and views were beautiful, and we loved spending time outside, especially sitting on the deck watching the beavers. The ..."
Reviewed on Aug 11, 2026
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.
Find the Best Windermere Vacation Packages
Windermere Essential Information
Language | English |
|---|---|
Currency | Canadian dollars |
Max Temp Winter | 25ºF |
Max Temp Summer | 75ºF |
Top Sights | Hardy Lake Provincial Park, Muskoka Lakes Winery and Aspen Valley Wildlife Sanctuary |
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Frequently asked questions
How much does a Windermere vacation package cost?
You can grab a vacation package to this destination from $1,051 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.
