Windermere vacation rentals

We found 439 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.

Vacation rentals with weekly discounts - Windermere

Showing deals for:Nov 7 - Nov 14

Image gallery for Cozy Muskoka Cottage Ideally located between Bracebridge and Port Carling

2 seating areas incl. a large loft w/ sectional, fireplace & TV on 2nd floor.
10 out of 10 rating
Exceptional
(8 reviews)

Cozy Muskoka Cottage Ideally located between Bracebridge and Port Carling

Muskoka Lakes, ON

24% off
Price is $317
$2,216 for 7 nights
All fees included
Cozy Muskoka Cottage Ideally located between Bracebridge and Port Carling

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Find out more about Windermere

Find out more about Windermere

Why visit Windermere

  1. Scenic Lakes and Islands: Explore breathtaking lakes and picturesque islands, perfect for outdoor adventures.
  2. Outdoor Activities: Enjoy golf, tennis, and various outdoor activities suitable for all ages.
  3. Charming Accommodations: Choose from cozy cottages, rustic cabins, and beautiful lakefront hotels.
  4. Romantic Ambiance: Experience a serene and romantic atmosphere ideal for couples and families alike.
  5. Friendly Local Community: Engage with welcoming locals and discover hidden gems throughout the region.

Popular types of accommodation in Windermere

If you're exploring vacation rentals in Windermere, you're in for a treat! Our most popular accommodations include charming cottages, spacious houses, and cozy cabins. Whether you’re looking for a lakeside retreat at a Muskoka resort, a relaxing stay at a Windermere house resort, or a serene lakefront hotel, we have a variety of options to suit your needs. Experience the beauty of Windermere with the perfect place to unwind!

  • Cottages: The top choice for vacation rentals in Windermere, offering cozy, homey accommodations surrounded by nature.
  • Houses: A great option for groups or families, providing spacious and fully-equipped homes for a relaxing stay.
  • Cabins: Charming and rustic, these rentals give you a true escape into the wilderness with easy access to outdoor activities.
  • Condos: Modern and convenient, these rentals offer a mix of comfort and amenities, perfect for a stylish getaway.
  • Apartments: Ideal for solo travelers or couples, offering compact and practical living spaces in the heart of Windermere.**

Top attractions in Windermere

Windermere, nestled in the scenic Muskoka Lakes region of Ontario, offers a perfect getaway for outdoor enthusiasts and romantics alike. Explore stunning lakes and islands while enjoying activities like golf, outdoor tennis, and the Magic of Muskoka. With various golf packages available, you'll find plenty of opportunities to relax and soak in the breathtaking scenery. Whether you're traveling solo, as a couple, or with family, Windermere promises a memorable vacation experience.

  1. Lake Rosseau: A serene and romantic lake perfect for outdoor activities, featuring beautiful beaches and stunning scenery, just 3 miles from Windermere.
  2. The Port Carling Wall: A cultural monument that reflects the rich history of the region, located 3 miles away and offering a glimpse into local heritage.
  3. Dee Bank Falls: An adventurous waterfall surrounded by nature, providing a romantic atmosphere and outdoor exploration, situated 2 miles from Windermere.

Things to do recommended for couples

Looking for a romantic getaway in Windermere? Explore the Muskoka Lakes Winery for wine tasting and enjoy the charming ambiance. For a bit of adventure, head to Muskoka Sports and Recreation for thrilling water activities, perfect for couples seeking excitement together.

Things to do recommended for families

Your family will have a blast at High Falls Water Park, just 13 miles from Windermere, with thrilling slides and pools. For a more relaxing experience, visit the Bracebridge Resource Management Centre, located 12 miles away, perfect for unwinding in nature.

Things to do recommended for groups

In Windermere, your group can enjoy a round of golf at Windermere Golf & Country Club, savor craft beers at Muskoka Brewery 16 miles away, and experience culture at the Gravenhurst Opera House, located 19 miles from Windermere, for a delightful mix of entertainment and romance.

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

If you're traveling with a group, with family, bringing along your pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Windermere with a group: Think about how many bedrooms you'll require, along with additional features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Windermere with young kids: Traveling with little ones can be quite demanding. It’s important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is a wise choice.
  • Taking your pets with you to Windermere: For many families, a trip wouldn't feel complete without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Many 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 that offer 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 options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Windermere

Windermere, nestled in the heart of Muskoka Lakes, offers an enchanting escape for those seeking a blend of outdoor adventure and serene beauty. Explore the stunning Muskoka District, unwind at charming beach resorts, and embrace the romantic ambiance of this picturesque region. With friendly locals and secluded spots, every corner invites relaxation and family-friendly fun. Discover the breathtaking scenery of Beautiful Muskoka and create unforgettable memories in this idyllic setting.

  • Huntsville: Located approximately 20 miles from Windermere, Huntsville is a vibrant city known for its stunning natural beauty and outdoor adventures. This area is perfect for those seeking a mix of excitement and tranquility. Popular activities include skiing in the winter and golfing in the warmer months, with numerous resorts offering excellent amenities. Don't miss exploring the nearby national parks and lakes, where you can hike, bike, or simply enjoy the breathtaking scenery. Huntsville's charming downtown area features local shops and restaurants, making it an ideal stop for a leisurely day out.
  • Port Carling: Just 4 miles from Windermere, Port Carling is a quaint village celebrated for its romantic atmosphere and picturesque landscapes. Visitors flock here for outdoor adventures, particularly golfing at its scenic courses and enjoying the serene lakeside views. The town is often referred to as the "Hub of the Muskoka Lakes," making it a convenient base for exploring the surrounding natural beauty. With its charming boutiques and waterfront parks, Port Carling offers a peaceful retreat where couples and families alike can relax and unwind.
  • Minett: Situated 5 miles away from Windermere, Minett is a hidden gem known for its lush scenery and romantic vibes. This small town is an outdoor enthusiast's paradise, offering activities like golfing and skiing at nearby resorts. The close proximity to national parks and beautiful lakes allows visitors to immerse themselves in nature, whether it's through hiking, fishing, or simply enjoying a picnic by the water. Minett's tranquil atmosphere and stunning vistas make it a perfect spot for couples looking to escape the hustle and bustle.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January16.7°F (-8.5°C)Light RainVery CloudyAverageSlightly High
February17.8°F (-7.9°C)Light RainVery CloudyAverageSlightly Low
March27.5°F (-2.5°C)Light RainMostly CloudyAverageAverage
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 HighAverage
July67.5°F (19.7°C)Light RainMostly SunnyModerately HighAverage
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 LowSlightly Low
December25.3°F (-3.7°C)Light RainMostly CloudyModerately LowSlightly High

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on the whole booking. It truly benefits you to take on the planning role! When you join our travel rewards program, One Key, you’ll gain access to exclusive discounts and accumulate OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, continue from where you last stopped, or manage your travel arrangements. You’ll discover your saved or booked properties neatly organized into categories such as Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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

How much does it cost to rent a vacation rental in Windermere?
Season, property type and length of stay are some of the things that can affect the price of a vacation home. Simply enter your travel dates to find the ultimate escape. From quaint country cottages to sprawling luxury villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Windermere?
Prices for beach houses in Windermere vary depending on the style and size of the property and when you plan to travel. All you have to do is enter your travel dates into Vrbo and how many guests to view your options and prices. From there you can use our filter tool to tailor your search by amenities, nearby activities, ratings and more.
How old do you have to be to rent a vacation rental in Windermere?
The minimum age requirements can differ between properties on Vrbo, so be sure to check the rules of the vacation home in Windermere you want to book. But normally, it's 16, 18 or 21.
How long can I rent a vacation rental in Windermere for?
It all depends on the Windermere property. To view a list of options offering extended stays, simply type your travel dates and number of guests into Vrbo's search page. Look forward to having the property to yourself, along with amenities such as a full kitchen, air conditioning and an outdoor space where the kids can run and play. Keep your eyes open for long-term stays that offer weekly or monthly discounts.
Does Vrbo offer discounts for vacation homes in Windermere?
In Windermere, you'll find some incredible discounts and deals for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you're off on a short getaway or a few weeks away, we've got a host of options to match your style.