Windermere Vacations from $762

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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.
Tay Motel

Tay Motel

2.5 out of 5
Price was $819, price is now $762 per person
$762
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Muskoka (YQA)
8.6/10 Excellent! (51 reviews)
I love this spot and have stayed here twice now. Super friendly owners and easy location right off the 400. The room has everything I need, and I have always had a good sleep. Recommended!

Reviewed on Jun 25, 2026

Rocky Crest Golf Resort

Rocky Crest Golf Resort

4 out of 5
Price was $1,232, price is now $1,067 per person
$1,067
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Muskoka (YQA)
8.2/10 Very Good! (394 reviews)
Lake view, staff, clean room

Reviewed on Jun 25, 2026

Muskoka Lake Cottages

Muskoka Lake Cottages

3 out of 5
Price was $1,228, price is now $1,160 per person
$1,160
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Muskoka (YQA)
7.6/10 Good! (114 reviews)
Nice location, clean room, friendly environment good management.

Reviewed on Jun 14, 2026

Windermere House

Windermere House

3.5 out of 5
Price was $1,337, price is now $1,263 per person
$1,263
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Muskoka (YQA)
9/10 Wonderful! (1,012 reviews)
We really enjoyed our stay! The breakfast spread was impressive and delicious. The pool area was beautiful and kept at 85, a perfect temperature. The grounds and hotel are lovely. The room was beautiful. Staff friendly, welcoming and accommodating. Pub restaurant food was excellent. We'll be back!

Reviewed on Jun 23, 2026

Terrawoods Resort Muskoka

Terrawoods Resort Muskoka

2 out of 5
Price was $1,198, price is now $1,157 per person
$1,157
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Muskoka (YQA)
7.6/10 Good! (10 reviews)
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Stay near popular Windermere attractions

Windermere Golf & Country Club

8.8/5 (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.
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What to do in Windermere

Private 4 Day Algonquin Park Backcountry Canoe Trip

Private 4 Day Algonquin Park Backcountry Canoe Trip

$1,084
per adult
Private 4 Day Algonquin Park Backcountry Canoe Trip
See all activities in Windermere

Windermere Hotel Deals

Windermere House

Windermere House

3.5 out of 5
2508 Windermere Road Muskoka Lakes ON
Fully refundableReserve now, pay when you stay
$275 nightly
The price is $311 total per night from Jun 28 to Jun 29
$311 total
Jun 28 - Jun 29
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"great place"

Reviewed on Jun 23, 2026

Windermere House
Charming Muskoka Wilderness Cottage

Charming Muskoka Wilderness Cottage

Windermere ON
9.8/10 Exceptional! (7 reviews)
"The cottage was modern and clean as advertised. It has everything you need in kitchen to cook meals or BBQ on deck. It is able to accommodate a family of 4 with extra bedroom. Communication was good with host ."

Reviewed on Jun 14, 2026

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Charming Muskoka Wilderness Cottage
Muskoka Tiny Home

Muskoka Tiny Home

Windermere ON
9.6/10 Exceptional! (4 reviews)
"This tiny home has everything you need for a cozy stay. It’s just like the pictures, there’s a beach 15-20 minutes away, and a market right around the corner for snacks and refrigerated goods. We had to go out for dinner one of the nights due to a power outage that affected the area we were in. Next ..."

Reviewed on May 31, 2026

Get rates
Muskoka Tiny Home
See all 1,063 properties in Windermere
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 $762 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.