Windermere Holidays

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Top hotels in Windermere

Windermere House
Windermere House
3.5 out of 5
2508 Windermere Road, Muskoka Lakes, ON
The price is S$412 per night from 13 Jul to 14 Jul
S$412
13 Jul - 14 Jul
includes taxes & fees
8.8/10 Excellent! (725 reviews)
"Nice place to enjoy the outdoors"

Reviewed on 28 Jun, 2025

Windermere House
Tru By Hilton Bracebridge, On
Tru By Hilton Bracebridge, On
2.5 out of 5
320 Taylor Road, Bracebridge, ON
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 7 Jul to 8 Jul
S$247
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (104 reviews)
"We were pleasantly surprised at how clean and modern Tru was. Staff was very helpful and inviting. We would definitely stay again."

Reviewed on 28 Jun, 2025

Tru By Hilton Bracebridge, On
JW Marriott The Rosseau Muskoka Resort & Spa
JW Marriott The Rosseau Muskoka Resort & Spa
4.5 out of 5
1050 Paignton House Road, Muskoka Lakes, ON
Fully refundableReserve now, pay when you stay
The price is S$737 per night from 9 Jul to 10 Jul
S$737
9 Jul - 10 Jul
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Really good"

Reviewed on 29 Jun, 2025

JW Marriott The Rosseau Muskoka Resort & Spa
See all 1,013 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.

Frequently asked questions

How much does a Windermere holiday package cost?
You can grab a holiday package to this destination on Expedia. But how much your holiday 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?
Plan your trip for the off-peak season and you're likely to score cheap Windermere holiday packages. Bear in mind that public holidays and local events and festivals can have an impact on prices, so do your research before booking.
How many days is enough for Windermere?
The ideal duration of your Windermere holiday depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to check out all the leading attractions and explore some hidden gems along the way.
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 personalise your search by "Amenities," "Property type," "Traveller 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 holiday as a package?
Expedia holiday 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 personalised Windermere holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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.
How to plan a trip to Windermere?

  1. Pick your travel dates: The things you plan to do in Windermere and your favourite season can help you decide when to get away.
  2. Plan your budget wisely: In addition to the cost of your accommodation, you should factor in other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that could arise during your trip to Windermere.
  3. Work out your trip length: Consider how much time you'd like to spend exploring Windermere. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Windermere holiday package that brings all your bookings together.

Popular places to visit

Diamond In The Ruff Golf Course

Enjoy a round of golf in Utterson at Diamond In The Ruff Golf Course. Amble around this family-friendly area's lakeside or seek out the canoeing opportunities.

Diamond In The Ruff Golf Course

What to do in Windermere

Muskoka Ultimate Adventure

Muskoka Ultimate Adventure

S$185
per adult
Muskoka Ultimate Adventure
See all activities in Windermere

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.