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Windermere Summer Rentals, Cottages & Cabins
Book a Place to Stay in Windermere for Your Summer Getaway
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- Balcony/Terrace
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- Pet Friendly
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- Designated Smoking Area
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- Pool
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- Pet Friendly
- TV
- Air Conditioner
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- Pet Friendly
- Air Conditioner
- TV
- View
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- TV
- Balcony/Terrace
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
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- Pet Friendly
- Air Conditioner
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- Pet Friendly
- Air Conditioner
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- Pet Friendly
- Air Conditioner
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- TV
- Air Conditioner
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- Pet Friendly
- Air Conditioner
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- Pet Friendly
- Air Conditioner
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- Pet Friendly
About Windermere Summer Rental on Trip The Film
With 79 summer rentals in or near Windermere, choosing a suitable rental home for your upcoming summer getaway on Trip The Film is easy. Whether you are traveling with family, friends, or in a group to Windermere or areas nearby, Trip The Film has plenty of summer accommodations to choose from, many with top amenities such as private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxury bedrooms, bathtubs, and pet-allowed environments.
Looking for a relaxing place to stay in Windermere for a summer vacation you do not want to forget easily? Trip The Film summer rental homes are available to provide you with the maximum comfort you deserve. Whether you're needing a unique style condo, luxury resort, villas, bungalow, cozy cabin, RV, or cottage in Windermere, Trip The Film has got you covered for your next summer holiday.
Frequently Asked Questions About Windermere Summer Rental
What are the top rated Summer Rentals in Windermere?
There are a lot of options in Windermere. If you plan on staying in the Windermere area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Windermere:
- Muskoka Manor, Windermere, Lake Rosseau, with Sauna and Fireplace
- 200 ft Private Muskoka waterfront custom log home with Hot Tub!
- Shea Lakehouse on Three Mile Lake, Muskoka
- Log home & guest cottage in old forest, Waterfall, Sunsets, Sauna, Fishing Boat
- Muskoka Gem with Sauna on Three Mile Lake
- MUSKOKA-L ROSSEAU.Water front cottage with use of Windermere Resort amentities
- SHEA HOUSE MUSKOKA Waterfront Lake House On Beautiful Three Mile Lake
- Cozy Getaway on Three Mile Lake
- Stunning Muskoka Waterfront Cottage on 3 Mile Lake!
- Lake Rosseau Muskoka, Monthly Rental 5mintoWindermere boat/trailerparking
How many summer rentals are available around Windermere, ON?
In 2026, Tripthefilm offers 79 summer rentals in or around Windermere. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
How much does it cost to rent a summer rental in Windermere?
The average price per night for a summer rental in Windermere is $881. Check the full list of summer accommodations in Windermere.
How many summer rentals are available to book in Windermere?
There are 79 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Tripthefilm.
Do any summer rentals in Windermere have a private pool?
Yes, here are some popular summer holiday rentals in Windermere that have a private or indoor pool:
- Private Muskoka cottage on 5 acres with 300 ft of waterfront
- Muskoka Shores Cottages
- Windermere House
- Lake Rosseau - The Heart of Muskoka - 5 mins to Port Carling
Check all holiday rentals with a pool in Windermere on Tripthefilm.