Windermere Summer Rentals, Cottages & Cabins

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
• Muskoka Gem with Sauna on Three Mile Lake
• Waterfront Lake House On Beautiful Three Mile Lake
• Cozy Getaway on Three Mile Lake
• Log home & guest cottage in old forest, Waterfall, Sunsets, Sauna, Fishing Boat
• Stunning Muskoka Waterfront Cottage on 3 Mile Lake!
• Lake Rosseau Muskoka, Monthly Rental 5mintoWindermere boat/trailerparking
• Beach House: Lake Rosseau Retreat with Private Beach, Hot Tub & Putting Green

In 2026, Cottagefarmhouse offers 78 summer rentals in or around Windermere. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.

The average price per night for a summer rental in Windermere is $858. Check the full list of summer accommodations in Windermere.

There are 78 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Cottagefarmhouse.

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 Cottagefarmhouse.