Deals on vacations and trips to Windermere

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Windermere flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Tay Motel

Tay Motel

2.5 out of 5
Price was $792, price is now $712 per person
$712
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Muskoka (YQA)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.
Windermere House

Windermere House

3.5 out of 5
Price was $1,175, price is now $1,044 per person
$1,044
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Muskoka (YQA)
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free resort. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like full breakfast and free self parking. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
Casa Albanese on Farlain Lake

Casa Albanese on Farlain Lake

2 out of 5
Price was $1,344, price is now $1,200 per person
$1,200
per person
Nov 22 - Nov 28
found 22 hours ago
Roundtrip flight included
Tampa (TPA) to Muskoka (YQA)
This cottage features barbecue grills. Take advantage of the free self parking.
The Dudley Inn

The Dudley Inn

2.5 out of 5
Price was $992, price is now $888 per person
$888
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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.
Sandy Lane Resort

Sandy Lane Resort

3 out of 5
Price was $1,268, price is now $1,144 per person
$1,144
per person
Nov 22 - Nov 28
found 21 hours ago
Roundtrip flight included
Tampa (TPA) to Muskoka (YQA)
A private beach and a restaurant are featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. Barbecue grills are provided for your convenience.

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
$146 nightly
The price is $165 total per night
$165 total
Nov 8 - Nov 9
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free resort. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like full breakfast and free self parking. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
Pool
Hot Tub
Muskoka Tiny Home

Muskoka Tiny Home

Windermere ON
Get rates
This cabin features laundry facilities.
Kitchen
Washer
3 Mile Lakehouse

3 Mile Lakehouse

Utterson ON
$442 nightly
The price is $500 total per night
$500 total
Oct 15 - Oct 16
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.
Kitchen
Pet friendly
Charming Muskoka Wilderness Cottage

Charming Muskoka Wilderness Cottage

Windermere ON
Get rates
This cottage featured laundry facilities and barbecue grills.
Kitchen
Washer
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
$177 nightly
The price is $203 total per night
$203 total
Oct 15 - Oct 16
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
Home2 Suites by Hilton Huntsville

Home2 Suites by Hilton Huntsville

3 out of 5
159 Howland Drive Huntsville ON
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $140 total per night
$140 total
Nov 13 - Nov 14
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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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.
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Frequently asked questions

How much are vacation packages to Windermere?
Travelocity has great package deals to Windermere, including flights and hotels, from an impressive $712. 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

A lake with boats, a grassy area with people, and mountains in the background.