Windermere vacation rentals

We found 452 vacation rentals — enter your dates for availability

Discover a selection of 16 cottages and other vacation rentals in Windermere that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the amenities you need and want for your stay, which might include parking and a fireplace. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about Windermere

Why visit Windermere

  • Stunning lake access: Enjoy breathtaking views and activities on the beautiful lakes surrounding Windermere.
  • Charming village atmosphere: Experience the friendly vibe and local charm of Windermere's quaint community.
  • Outdoor activities: Engage in hiking, biking, and water sports amidst the picturesque Muskoka landscape.
  • Romantic getaways: Perfect for couples, with cozy accommodations and idyllic settings for relaxation.
  • Family-friendly attractions: Discover nearby theme parks and historical museums that cater to all ages.

Popular types of accommodation in Windermere

If you're exploring vacation rentals in Windermere, you have plenty of fantastic options. Our most popular accommodations include charming cottages, spacious houses, and cozy cabins. Many properties offer convenient amenities like room service, laundry facilities, and select hotel features. Discover the best rentals that suit your needs, ensuring a comfortable and enjoyable stay in this beautiful destination.

  • Cottages: The top choice for vacation rentals in Windermere, offering a cozy and charming retreat amidst nature.
  • Houses: A popular option for families or groups seeking spacious accommodations with home-like amenities.
  • Cabins: Ideal for those looking for a rustic getaway, cabins provide a unique and intimate experience.
  • Condos: Perfect for travelers wanting modern conveniences with access to amenities and beautiful views.
  • Chalets: A favorite among those wanting a blend of comfort and alpine charm in a picturesque setting.**

Top attractions in and around Windermere

Windermere, Muskoka Lakes, Ontario, is an ideal destination for outdoor enthusiasts and couples seeking a romantic getaway. With its stunning lakes, charming theme parks, and intriguing history museums, there’s something for everyone. Whether you're looking to relax on the beach or explore the scenic surroundings, Windermere offers a variety of attractions that will enhance your vacation experience, making it a perfect spot for memorable adventures.

  • Windermere Golf & Country Club: Experience a family-friendly atmosphere with a relaxing vibe at this beautiful golf course. Enjoy lush greens and stunning views, perfect for a day of golf or a leisurely stroll.
  • Lake Muskoka: Located 10 miles away, this picturesque lake offers outdoor adventures, sandy beaches, and romantic scenery. It's an ideal spot for swimming, kayaking, or simply soaking up the sun.
  • Santa's Village: Just 13 miles from Windermere, this enchanting theme park provides endless entertainment for families. Enjoy festive rides, games, and activities that will delight visitors of all ages.

Things to do recommended for couples

Windermere in Muskoka Lakes offers a perfect romantic getaway. Enjoy a sunset cruise on the tranquil waters, explore charming local shops, or indulge in a couples' spa day. Don't forget a cozy dinner at a lakeside restaurant for a memorable evening together.

Things to do recommended for families

Families will love exploring the scenic trails around Windermere, enjoying boating on the beautiful Muskoka Lakes, or visiting the charming local shops. Don't miss the fun at the nearby Muskoka Discovery Centre, where kids can learn about the area's history and culture through interactive exhibits.

Things to do recommended for groups

Explore the beauty of Muskoka on a group boat tour, relax at the Windermere Marina, or indulge in a wine tasting at a local vineyard. Don’t miss hiking the scenic trails at nearby parks for stunning views and memorable experiences with friends.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Windermere

No matter if you're traveling with friends, family, pets, or planning an extended stay, it's important to prioritize your preferences when filtering your options. Here are some helpful booking tips for using Vrbo.

  • Traveling to Windermere with a group: Think about how many bedrooms you'll require, as well as any amenities you might want, like a full kitchen or outdoor space for gatherings. Luckily, you can easily filter for these features and more on Vrbo.
  • Traveling to Windermere with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, you should think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windermere: For many families, a trip wouldn’t be the same without their beloved pet by their side. If you can relate, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windermere: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Windermere

Windermere, nestled in the stunning Muskoka Lakes region, offers a charming escape for outdoor enthusiasts and couples seeking romance. With its beautiful lake access and the backdrop of rocky mountains, you'll find the perfect blend of relaxation and adventure. Explore the friendly village atmosphere or venture into nearby neighborhoods for family-friendly activities and secluded spots. This convenient location is ideal for an unforgettable Muskoka getaway, where every moment is filled with scenic beauty and rich history.

  • Muskoka Lakes: Muskoka Lakes is renowned for its stunning natural beauty and outdoor adventures. Nestled in the heart of Ontario's cottage country, this city offers breathtaking lake views, lush forests, and picturesque landscapes. Visitors are drawn to Muskoka Lakes for its romantic atmosphere and opportunities for skiing, golfing, and enjoying luxurious resort amenities. Key attractions include pristine lakes and the nearby national and state parks, perfect for hiking, picnicking, and nature exploration. Whether you're looking to unwind at a lakeside cabin or engage in outdoor activities, Muskoka Lakes provides an unforgettable experience.
  • Port Carling: Just 4 miles from Windermere, Port Carling is a charming village known as the Hub of the Muskoka Lakes. This picturesque destination offers a delightful mix of outdoor activities and scenic beauty. With its golf courses and resorts, Port Carling is perfect for both relaxation and recreation. The area is surrounded by stunning lakes and parks, making it an ideal spot for boating, fishing, and enjoying nature walks. Visitors can also explore local shops and eateries, adding to the village's quaint charm.
  • Minett: Located 5 miles from Windermere, Minett is a delightful village that captures the essence of Muskoka's outdoor lifestyle. Known for its beautiful landscapes and recreational opportunities, Minett attracts visitors seeking adventure and tranquility. Enjoy golf at scenic courses or relax at nearby resorts. With access to stunning lakes and the thrill of a theme park, Minett offers something for everyone. Whether you're looking for thrilling activities or a peaceful retreat, this village is a perfect addition to your Muskoka experience.

Best time to go to Windermere

If you're planning a trip to Windermere, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January16.7°F (-8.5°C)Light RainVery CloudyAverageAverage
February17.8°F (-7.9°C)Light RainVery CloudyAverageSlightly Low
March27.5°F (-2.5°C)Light RainMostly CloudyAverageSlightly Low
April39.4°F (4.1°C)Light RainMostly CloudyAverageSlightly Low
May53.6°F (12.0°C)Light RainMostly SunnyAverageAverage
June61.7°F (16.5°C)Light RainMostly SunnyModerately HighSlightly High
July67.5°F (19.7°C)Light RainMostly SunnyModerately HighSlightly High
August66.0°F (18.9°C)Light RainMostly SunnyModerately HighSlightly High
September59.2°F (15.1°C)Light RainMostly SunnyAverageAverage
October47.5°F (8.6°C)Light RainMostly CloudyModerately LowAverage
November35.4°F (1.9°C)Light RainMostly CloudyModerately LowAverage
December25.3°F (-3.7°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's user-friendly Trip Board offers you a dedicated space to plan new trips, pick up right where you left off, or manage and organize your travel plans. You can easily find properties you've saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Recharge in Windermere

Windermere is situated in the warm and welcoming heart of Muskoka, a picture-perfect district in Ontario. Set beside the lake amid sprawling forests and unspoiled landscapes, it's a haven for rest and recreation in equal measure. From tranquil woodland walks and calming cruises on the lake, to fishing, cross-country skiing and dogsledding, the area offers year-round activities for everyone. After an outdoorsy day, Windermere vacation rentals, which range from cottages to lavish lakeside digs, offer creature comforts aplenty.

Windermere's Victorian gem

Windermere Marina is the epicenter of the community's water recreation. Situated on Lake Rosseau, it's the go-to for boat rentals and water taxis to surrounding islands, and features a gift shop and restaurant. For golfers, it doesn't get much better than the Windermere Golf and Country Club. Bordered by granite outcroppings and white pine trees, the 18-hole championship course should appeal to inexperienced and seasoned players alike. The community's historic jewel is Windermere House, a stately white Victorian pile nestled in mature lakeside grounds. Originally built as a boarding house, it now serves as a hotel and popular wedding venue.

Scenic seasons in Windermere

Whenever you're booking your Windermere vacation rental, there are activities for every season. If you're here for snow-based fun, then Muskoka's bone-chillingly cold winters ensure there's plenty of snow on the ground. If you're here for the scenery, the region is probably most attractive during the fall, when its trees take on fiery bronze hues. Summer is often the most popular time for outdoorsy folk to visit, however - with average high temperatures reaching a very warm 77 in July.

Be inspired by Windermere's breathtaking beauty

With its glinting lakes, rock-studded shores and sprawling undisturbed forests, Muskoka provides Windermere with a spectacular backyard – and it's little surprise that artists, photographers, nature lovers and birdwatchers all come to be inspired. Large swathes of its unspoiled landscape are contained within the region's 11 provincial parks, as well as its prized natural attraction - Georgian Bay Island National Park. Alongside the endless activities they offer, they provide a habitat for a menagerie of local creatures, from deer and moose to a variety of Canadian birds.

Traveling to and around Windermere

The nearest airport is in Muskoka, ON (YQA), located 18.1 mi (29.1 km) from the city center.

Frequently asked questions

What is the best area to stay in Windermere, Ontario, Canada when booking a vacation rental?
In Windermere, Ontario, one of the best areas to consider for a vacation rental is the picturesque neighborhood surrounding the lake itself. This area offers stunning views and easy access to outdoor activities, making it ideal for nature enthusiasts and families alike. You can enjoy kayaking, paddleboarding, or simply relaxing by the water, which adds to the charm of your stay.

Another appealing aspect of this neighborhood is its proximity to local attractions, such as the scenic trails and parks that invite exploration and adventure. Nearby, you can also find quaint shops and dining options that reflect the local culture, ensuring a delightful blend of relaxation and discovery during your visit. The availability of vacation rentals in this area is quite good, offering a range of choices to suit different preferences and budgets.
How much does it cost to rent a vacation home in Windermere?
Prices for vacation rentals in Windermere vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windermere to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Windermere vacation house rentals?
You can find great discounts on house rentals in Windermere on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay vacation rentals in Windermere?
A long-stay vacation rental in Windermere is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Windermere vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Windermere with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Windermere for a vacation rental?
The best time to visit Windermere for a vacation rental is during the peak summer season from June to August, with July being the most popular month. This period attracts travelers eager to enjoy the stunning landscapes and outdoor activities that Windermere has to offer. With warm temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, visitors can indulge in swimming, hiking, and exploring the beautiful Ontario countryside.

July brings a vibrant setting as families, couples, and adventure seekers flock to the area. The long days filled with sunshine provide a great backdrop for boating on the serene waters or taking leisurely strolls through charming local shops and eateries. This is also an ideal time to partake in community events and festivals that showcase local culture and food.

For those looking for a more budget-friendly option, November can be a great time to visit Windermere. Although it's outside the main tourist season, the crisp autumn air and beautiful fall foliage create a picturesque setting great for cozy getaways. This quieter month allows visitors to savor the beauty of nature without the hustle and bustle of peak season.

Ultimately, your choice will depend on whether you prefer the lively summer atmosphere filled with activities or the tranquil beauty of autumn's colors.
How early should I book a Windermere vacation rental?
Book your Windermere vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Windermere, Ontario, Canada?
In Windermere, Ontario, visitors can enjoy a picturesque escape with a wealth of attractions. The area is renowned for its stunning natural beauty, with Lake Rosseau and Lake Joseph providing opportunities for boating, fishing, and swimming. The Windermere House, a historic hotel, is a prominent landmark and offers tours showcasing its rich history, as well as dining options with beautiful lake views.

Outdoor enthusiasts can explore the nearby Muskoka Lakes region, famous for its hiking trails and scenic landscapes. The local area features charming shops and cafes that reflect the cozy, rustic vibe of cottage country.
Can I change or cancel my Windermere home rental booking on Vrbo?
To find Windermere vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Windermere vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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