Deals on vacations and trips to Windermere

Save when you book Windermere package deals

Choose two or more items and save on your trip:

Windermere flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sunnylea Resort

Sunnylea Resort

2.5 out of 5
Price was $437, price is now $405 per person
$405
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Muskoka (YQA)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this holiday park. WiFi in public areas is free. A picnic area is also provided.
Rocky Crest Golf Resort

Rocky Crest Golf Resort

4 out of 5
Price was $628, price is now $558 per person
$558
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Muskoka (YQA)
This smoke-free resort features a golf course, free water park access, and 3 restaurants. Dine at the beachfront restaurant and relax with sun loungers. There's fun for all ages with a children's pool and a playground, and babysitting is an added bonus.
Touchstone Resort

Touchstone Resort

4 out of 5
Price was $631, price is now $561 per person
$561
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Muskoka (YQA)
This smoke-free aparthotel features a private beach, a full-service spa, and a restaurant. A seasonal outdoor pool, a gym, and a sauna are also on offer.
The Dudley Inn

The Dudley Inn

2.5 out of 5
Price was $554, price is now $504 per person
$504
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Muskoka (YQA)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-out and a virtual front desk are also provided.
Windermere House

Windermere House

3.5 out of 5
Price was $894, price is now $813 per person
$813
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Muskoka (YQA)
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free resort. Enjoy the 24-hour gym and free perks like full breakfast and free self parking. You'll appreciate the outdoor tennis court, bar/lounge, and wedding services.

Top Windermere hotels deals

Windermere House

Windermere House

3.5 out of 5
2508 Windermere Road Muskoka Lakes ON
Free Cancellation
Reserve now, pay when you stay
$262 nightly
The price is $296 total per night
$296 total
Sep 8 - Sep 9
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free resort. Enjoy the 24-hour gym and free perks like full breakfast and free self parking. You'll appreciate the outdoor tennis court, bar/lounge, and wedding services.
Pool
Hot Tub
Muskoka Tiny Home

Muskoka Tiny Home

Windermere ON
Get rates
This cabin features laundry facilities.
Kitchen
Washer
Charming Muskoka Wilderness Cottage

Charming Muskoka Wilderness Cottage

Windermere ON
Get rates
This cottage featured laundry facilities and barbecue grills.
Kitchen
Washer
3 Mile Lakehouse

3 Mile Lakehouse

Utterson ON
$450 nightly
The price is $509 total per night
$509 total
Sep 8 - Sep 9
Total with taxes and fees
Stay at this cottage in Muskoka Lakes. Enjoy air conditioning. Popular attractions Dee Bank Falls and Three Mile Lake are located nearby.
Pet friendly
Air conditioning
Last Two Weeks of Summer Available- Large Dock, Hot Tub, Beach w Water Toys

Last Two Weeks of Summer Available- Large Dock, Hot Tub, Beach w Water Toys

Utterson ON
Get rates
A hot tub is featured at this cottage, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.
Hot Tub
Kitchen
Muskoka Bay Resort

Muskoka Bay Resort

3.5 out of 5
1217 N Muldrew Lake Rd Gravenhurst ON
Free Cancellation
Reserve now, pay when you stay
$217 nightly
The price is $249 total per night
$249 total
Sep 8 - Sep 9
Total with taxes and fees
A golf course and a gym are featured at this hotel. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas.
Pool
Pet friendly
Don't see what you're looking for?
See all available properties in Windermere
View all properties
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.

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.
See properties

Frequently asked questions

How much are vacation packages to Windermere?
Travelocity has great package deals to Windermere, including flights and hotels, from an impressive $405. With all the money you save, you could book some cool tours or maybe add on a few extra nights to your getaway.
How long should my Windermere vacation be?
Many travelers choose to spend about 3 nights in Windermere, but it's totally up to you. If you intend to venture out and explore all the fantastic things this destination offers, why not hang around for a couple of extra nights?
Where can I get the best vacation package deals for Windermere?
There are exciting Windermere package deals to be snapped up with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties around the world? Keep that in mind the next time you're ready to cross another place off your bucket list.
Why should I book my Windermere vacation package via Travelocity?
By booking your flights, hotel, activities and car rental all in one place, you'll save big bucks as well as precious time. All our bookings come with a professional customer service support team available round-the-clock, and you'll know that you'll always score the best deal in town with our Price Match Guarantee. So, what's stopping you? Book that dream vacation today and start packing!
Can I save money on my Windermere car rental if I book it with a hotel or flight?
Bundling your car, hotel and flight into a Windermere vacation package is a surefire way to score better prices. Plus, having your own car rental gives you total freedom to make your way to all those big-name sights you're itching to check out. Located 90 mi from Windermere, Canadas Wonderland is one place that should be on your to-do list. Buckle up and make a day trip of it.
What is the best time of year to go to Windermere?
If a tight budget is what's driving your decision making, you'll score the best prices in . is the costliest time of year. Most people head here during February, July and August. If you want to avoid peak time, visit during September, November and December.
Where should I stay when visiting Windermere?
If you're looking for a place to lay your head, take a look at the Windermere House. It's the top pick for many visitors.

Photos of local treasures

Browse Windermere vacation photos for more inspiration